Bis(7-amino-2,4-dimethyl-1,8-naphthyridine)dinitratocadmium(II).

In the title compound, [Cd(NO(3))(2)(C(10)H(11)N(3))(2)], two naph-thyridine ring systems are coordinated to the Cd ion through the two N atoms in a bidentate chelating mode, whereas the remaining coordination sites are occupied by two O atoms from two different nitrate groups to complete the octahedral geometry. Inter-moleular N-H⋯O hydrogen bonds link the mol-ecules to form a one-dimensionnal sheet parallel to the ac plane. Weak slipped π-π stacking involving the naphthyridine ring systems stabilizes the structure.

Related literature

For related literature, see: Bayer (1979 ▶); Che et al. (2001 ▶); Gavrilova & Bosnich (2004 ▶); Jin et al. (2007 ▶); Kukrek et al. (2006 ▶); Mintert & Sheldrick (1995a ▶,b ▶); Oskui & Sheldrick (1999 ▶); Oskui, Mintert & Sheldrick (1999 ▶).

Experimental

Crystal data

[Cd(NO3)2(C10H11N3)2]

M = 582.86

Triclinic,

a = 9.308 (2) Å

b = 9.584 (2) Å

c = 15.067 (4) Å

α = 95.497 (3)°

β = 95.224 (3)°

γ = 116.865 (3)°

V = 1179.8 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.98 mm−1

T = 298 (2) K

0.45 × 0.37 × 0.31 mm

Data collection

Bruker SMART diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.667, T max = 0.751

6136 measured reflections

4101 independent reflections

3346 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.081

S = 1.09

4101 reflections

320 parameters

H-atom parameters constrained

Δρmax = 0.67 e Å−3

Δρmin = −0.36 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680706271X/dn2283sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680706271X/dn2283Isup2.hkl

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

[Cd(NO3)2(C10H11N3)2]	Z = 2
Mr = 582.86	F000 = 588
Triclinic, P1	Dx = 1.641 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 9.308 (2) Å	Cell parameters from 2793 reflections
b = 9.584 (2) Å	θ = 2.4–26.1º
c = 15.067 (4) Å	µ = 0.98 mm−1
α = 95.497 (3)º	T = 298 (2) K
β = 95.224 (3)º	Block, colorless
γ = 116.865 (3)º	0.45 × 0.37 × 0.31 mm
V = 1179.8 (5) Å3

Bruker SMART diffractometer	4101 independent reflections
Radiation source: fine-focus sealed tube	3346 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.019
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −11→6
Tmin = 0.667, Tmax = 0.751	k = −11→11
6136 measured reflections	l = −17→17

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035	H-atom parameters constrained
wR(F2) = 0.081	w = 1/[σ2(Fo2) + (0.037P)2 + 0.1524P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.004
4101 reflections	Δρmax = 0.67 e Å−3
320 parameters	Δρmin = −0.36 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
Cd1	0.32533 (3)	0.63678 (3)	0.248895 (17)	0.04168 (11)
N1	0.3847 (3)	0.7270 (3)	0.41178 (18)	0.0381 (7)
N2	0.5294 (3)	0.6210 (3)	0.34613 (18)	0.0385 (7)
N3	0.6662 (4)	0.5103 (4)	0.2720 (2)	0.0624 (10)
H3A	0.6026	0.4943	0.2228	0.075*
H3B	0.7418	0.4820	0.2719	0.075*
N4	0.5509 (4)	0.8962 (4)	0.2110 (2)	0.0448 (7)
N5	0.2822 (4)	0.8123 (3)	0.17237 (18)	0.0407 (7)
N6	0.0057 (4)	0.7107 (4)	0.1316 (2)	0.0616 (9)
H6A	−0.0097	0.6348	0.1619	0.074*
H6B	−0.0763	0.7152	0.1034	0.074*
N7	0.2627 (5)	0.4197 (4)	0.0808 (2)	0.0568 (9)
N8	0.0220 (4)	0.4282 (4)	0.3115 (2)	0.0459 (8)
O1	0.1458 (4)	0.4451 (4)	0.0924 (2)	0.0826 (10)
O2	0.3852 (4)	0.4845 (4)	0.1406 (2)	0.0784 (10)
O3	0.2607 (4)	0.3373 (4)	0.0126 (2)	0.0803 (10)
O4	0.1344 (3)	0.3951 (3)	0.29808 (18)	0.0550 (7)
O5	0.0207 (4)	0.5429 (4)	0.27969 (18)	0.0622 (8)
O6	−0.0832 (5)	0.3513 (4)	0.3543 (2)	0.0927 (11)
C1	0.5092 (4)	0.6900 (4)	0.4236 (2)	0.0342 (8)
C2	0.6476 (4)	0.5792 (4)	0.3489 (2)	0.0395 (8)
C3	0.7515 (4)	0.6041 (4)	0.4305 (2)	0.0447 (9)
H3	0.8323	0.5722	0.4311	0.054*
C4	0.7316 (4)	0.6744 (4)	0.5071 (2)	0.0427 (9)
H4	0.8013	0.6939	0.5603	0.051*
C5	0.6056 (4)	0.7189 (4)	0.5074 (2)	0.0361 (8)
C6	0.5702 (4)	0.7900 (4)	0.5826 (2)	0.0403 (8)
C7	0.4400 (5)	0.8216 (4)	0.5692 (2)	0.0449 (9)
H7	0.4116	0.8652	0.6181	0.054*
C8	0.3495 (4)	0.7898 (4)	0.4836 (2)	0.0386 (8)
C9	0.6701 (5)	0.8290 (5)	0.6740 (2)	0.0586 (11)
H9A	0.6225	0.8677	0.7177	0.088*
H9B	0.7791	0.9088	0.6724	0.088*
H9C	0.6725	0.7356	0.6902	0.088*
C10	0.2099 (5)	0.8259 (5)	0.4700 (3)	0.0533 (10)
H10A	0.1851	0.8294	0.4073	0.080*
H10B	0.2383	0.9266	0.5047	0.080*
H10C	0.1165	0.7451	0.4893	0.080*
C11	0.4365 (5)	0.9236 (4)	0.1670 (2)	0.0406 (8)
C12	0.1564 (5)	0.8210 (5)	0.1283 (2)	0.0470 (9)
C13	0.1818 (6)	0.9478 (5)	0.0788 (3)	0.0560 (11)
H13	0.0928	0.9539	0.0496	0.067*
C14	0.3334 (6)	1.0585 (5)	0.0741 (3)	0.0571 (11)
H14	0.3489	1.1410	0.0419	0.069*
C15	0.4704 (5)	1.0502 (4)	0.1182 (2)	0.0466 (9)
C16	0.6348 (6)	1.1545 (5)	0.1155 (3)	0.0545 (11)
C17	0.7501 (6)	1.1242 (5)	0.1602 (3)	0.0623 (12)
H17	0.8598	1.1908	0.1592	0.075*
C18	0.7068 (5)	0.9956 (5)	0.2072 (3)	0.0554 (10)
C19	0.6828 (6)	1.2936 (5)	0.0644 (3)	0.0732 (14)
H19A	0.7992	1.3479	0.0680	0.110*
H19B	0.6461	1.3648	0.0904	0.110*
H19C	0.6336	1.2561	0.0023	0.110*
C20	0.8329 (5)	0.9635 (6)	0.2569 (4)	0.0837 (15)
H20A	0.8194	0.9630	0.3193	0.126*
H20B	0.9396	1.0446	0.2521	0.126*
H20C	0.8206	0.8624	0.2313	0.126*

	U11	U22	U33	U12	U13	U23
Cd1	0.03665 (17)	0.05040 (19)	0.03889 (17)	0.02133 (13)	−0.00124 (11)	0.01172 (12)
N1	0.0334 (16)	0.0441 (18)	0.0397 (17)	0.0198 (15)	0.0055 (13)	0.0101 (14)
N2	0.0343 (16)	0.0515 (19)	0.0318 (16)	0.0219 (15)	0.0033 (13)	0.0070 (13)
N3	0.056 (2)	0.103 (3)	0.0426 (19)	0.053 (2)	0.0011 (16)	−0.0061 (19)
N4	0.0439 (19)	0.0461 (19)	0.0428 (18)	0.0198 (17)	0.0060 (15)	0.0060 (14)
N5	0.0465 (19)	0.0442 (18)	0.0313 (16)	0.0218 (16)	0.0004 (14)	0.0064 (13)
N6	0.047 (2)	0.072 (3)	0.064 (2)	0.026 (2)	−0.0057 (17)	0.0254 (19)
N7	0.076 (3)	0.057 (2)	0.041 (2)	0.037 (2)	−0.0073 (19)	0.0058 (17)
N8	0.0391 (18)	0.054 (2)	0.0418 (18)	0.0183 (17)	0.0073 (15)	0.0091 (16)
O1	0.083 (2)	0.101 (3)	0.081 (2)	0.061 (2)	0.0066 (19)	0.0053 (19)
O2	0.073 (2)	0.100 (3)	0.0541 (19)	0.044 (2)	−0.0205 (16)	−0.0151 (17)
O3	0.111 (3)	0.096 (3)	0.0524 (19)	0.077 (2)	−0.0252 (18)	−0.0190 (17)
O4	0.0460 (16)	0.0676 (19)	0.0608 (18)	0.0351 (15)	0.0044 (13)	0.0099 (14)
O5	0.072 (2)	0.071 (2)	0.0607 (18)	0.0446 (18)	0.0102 (15)	0.0249 (16)
O6	0.089 (3)	0.092 (3)	0.100 (3)	0.032 (2)	0.060 (2)	0.037 (2)
C1	0.0311 (18)	0.0372 (19)	0.0331 (19)	0.0152 (16)	0.0029 (15)	0.0069 (15)
C2	0.033 (2)	0.048 (2)	0.039 (2)	0.0206 (18)	0.0045 (16)	0.0052 (17)
C3	0.034 (2)	0.055 (2)	0.049 (2)	0.0253 (19)	−0.0001 (17)	0.0072 (19)
C4	0.035 (2)	0.050 (2)	0.039 (2)	0.0176 (18)	−0.0038 (16)	0.0045 (17)
C5	0.0343 (19)	0.0355 (19)	0.0347 (19)	0.0139 (17)	0.0013 (15)	0.0042 (15)
C6	0.041 (2)	0.039 (2)	0.037 (2)	0.0156 (18)	0.0013 (16)	0.0029 (16)
C7	0.048 (2)	0.042 (2)	0.043 (2)	0.0206 (19)	0.0096 (18)	0.0027 (17)
C8	0.0327 (19)	0.034 (2)	0.048 (2)	0.0130 (16)	0.0113 (17)	0.0103 (17)
C9	0.062 (3)	0.076 (3)	0.037 (2)	0.036 (2)	−0.0058 (19)	−0.006 (2)
C10	0.046 (2)	0.059 (3)	0.067 (3)	0.032 (2)	0.014 (2)	0.014 (2)
C11	0.050 (2)	0.037 (2)	0.0300 (19)	0.0172 (19)	0.0063 (17)	−0.0007 (15)
C12	0.057 (3)	0.052 (2)	0.035 (2)	0.029 (2)	0.0013 (18)	0.0076 (18)
C13	0.069 (3)	0.062 (3)	0.046 (2)	0.038 (3)	0.003 (2)	0.015 (2)
C14	0.090 (4)	0.051 (3)	0.041 (2)	0.040 (3)	0.013 (2)	0.0157 (19)
C15	0.067 (3)	0.038 (2)	0.034 (2)	0.023 (2)	0.0129 (19)	0.0019 (17)
C16	0.075 (3)	0.040 (2)	0.036 (2)	0.016 (2)	0.014 (2)	−0.0011 (18)
C17	0.059 (3)	0.053 (3)	0.060 (3)	0.013 (2)	0.018 (2)	0.002 (2)
C18	0.044 (2)	0.056 (3)	0.059 (3)	0.019 (2)	0.007 (2)	0.000 (2)
C19	0.097 (4)	0.043 (3)	0.057 (3)	0.011 (3)	0.028 (3)	0.009 (2)
C20	0.047 (3)	0.082 (4)	0.118 (4)	0.027 (3)	0.008 (3)	0.020 (3)

Cd1—N5	2.284 (3)	C4—H4	0.9300
Cd1—O2	2.355 (3)	C5—C6	1.408 (5)
Cd1—N2	2.361 (3)	C6—C7	1.379 (5)
Cd1—O4	2.433 (3)	C6—C9	1.501 (5)
Cd1—N1	2.448 (3)	C7—C8	1.400 (5)
Cd1—N4	2.586 (3)	C7—H7	0.9300
N1—C8	1.326 (4)	C8—C10	1.490 (5)
N1—C1	1.359 (4)	C9—H9A	0.9600
N2—C2	1.328 (4)	C9—H9B	0.9600
N2—C1	1.356 (4)	C9—H9C	0.9600
N3—C2	1.343 (4)	C10—H10A	0.9600
N3—H3A	0.8600	C10—H10B	0.9600
N3—H3B	0.8600	C10—H10C	0.9600
N4—C18	1.339 (5)	C11—C15	1.406 (5)
N4—C11	1.342 (5)	C12—C13	1.427 (5)
N5—C12	1.333 (4)	C13—C14	1.342 (6)
N5—C11	1.364 (5)	C13—H13	0.9300
N6—C12	1.330 (5)	C14—C15	1.422 (6)
N6—H6A	0.8600	C14—H14	0.9300
N6—H6B	0.8600	C15—C16	1.406 (6)
N7—O3	1.229 (4)	C16—C17	1.370 (6)
N7—O1	1.241 (4)	C16—C19	1.514 (5)
N7—O2	1.250 (4)	C17—C18	1.398 (6)
N8—O6	1.213 (4)	C17—H17	0.9300
N8—O5	1.246 (4)	C18—C20	1.498 (6)
N8—O4	1.250 (4)	C19—H19A	0.9600
C1—C5	1.405 (4)	C19—H19B	0.9600
C2—C3	1.423 (5)	C19—H19C	0.9600
C3—C4	1.351 (5)	C20—H20A	0.9600
C3—H3	0.9300	C20—H20B	0.9600
C4—C5	1.418 (5)	C20—H20C	0.9600
N5—Cd1—O2	104.91 (11)	C7—C6—C9	121.4 (3)
N5—Cd1—N2	140.76 (11)	C5—C6—C9	121.2 (3)
O2—Cd1—N2	84.14 (10)	C6—C7—C8	121.6 (3)
N5—Cd1—O4	130.94 (10)	C6—C7—H7	119.2
O2—Cd1—O4	89.68 (11)	C8—C7—H7	119.2
N2—Cd1—O4	86.30 (9)	N1—C8—C7	121.4 (3)
N5—Cd1—N1	111.10 (9)	N1—C8—C10	117.6 (3)
O2—Cd1—N1	139.39 (10)	C7—C8—C10	121.0 (3)
N2—Cd1—N1	56.05 (9)	C6—C9—H9A	109.5
O4—Cd1—N1	80.82 (9)	C6—C9—H9B	109.5
N5—Cd1—N4	54.63 (10)	H9A—C9—H9B	109.5
O2—Cd1—N4	91.13 (11)	C6—C9—H9C	109.5
N2—Cd1—N4	87.67 (10)	H9A—C9—H9C	109.5
O4—Cd1—N4	173.80 (9)	H9B—C9—H9C	109.5
N1—Cd1—N4	94.61 (9)	C8—C10—H10A	109.5
C8—N1—C1	118.2 (3)	C8—C10—H10B	109.5
C8—N1—Cd1	148.2 (2)	H10A—C10—H10B	109.5
C1—N1—Cd1	93.59 (19)	C8—C10—H10C	109.5
C2—N2—C1	118.5 (3)	H10A—C10—H10C	109.5
C2—N2—Cd1	143.8 (2)	H10B—C10—H10C	109.5
C1—N2—Cd1	97.6 (2)	N4—C11—N5	112.6 (3)
C2—N3—H3A	120.0	N4—C11—C15	124.2 (4)
C2—N3—H3B	120.0	N5—C11—C15	123.2 (3)
H3A—N3—H3B	120.0	N6—C12—N5	119.3 (3)
C18—N4—C11	117.4 (3)	N6—C12—C13	120.0 (4)
C18—N4—Cd1	152.3 (3)	N5—C12—C13	120.7 (4)
C11—N4—Cd1	89.8 (2)	C14—C13—C12	120.4 (4)
C12—N5—C11	119.0 (3)	C14—C13—H13	119.8
C12—N5—Cd1	137.6 (3)	C12—C13—H13	119.8
C11—N5—Cd1	102.9 (2)	C13—C14—C15	120.3 (4)
C12—N6—H6A	120.0	C13—C14—H14	119.8
C12—N6—H6B	120.0	C15—C14—H14	119.8
H6A—N6—H6B	120.0	C11—C15—C16	117.8 (4)
O3—N7—O1	121.8 (4)	C11—C15—C14	116.3 (4)
O3—N7—O2	120.9 (4)	C16—C15—C14	125.9 (4)
O1—N7—O2	117.3 (3)	C17—C16—C15	117.4 (4)
O6—N8—O5	120.6 (3)	C17—C16—C19	121.2 (4)
O6—N8—O4	121.3 (4)	C15—C16—C19	121.5 (4)
O5—N8—O4	118.1 (3)	C16—C17—C18	121.5 (4)
N7—O2—Cd1	105.8 (3)	C16—C17—H17	119.2
N8—O4—Cd1	100.6 (2)	C18—C17—H17	119.2
N2—C1—N1	112.7 (3)	N4—C18—C17	121.8 (4)
N2—C1—C5	123.7 (3)	N4—C18—C20	116.7 (4)
N1—C1—C5	123.5 (3)	C17—C18—C20	121.6 (4)
N2—C2—N3	118.1 (3)	C16—C19—H19A	109.5
N2—C2—C3	121.8 (3)	C16—C19—H19B	109.5
N3—C2—C3	120.1 (3)	H19A—C19—H19B	109.5
C4—C3—C2	119.3 (3)	C16—C19—H19C	109.5
C4—C3—H3	120.4	H19A—C19—H19C	109.5
C2—C3—H3	120.4	H19B—C19—H19C	109.5
C3—C4—C5	120.7 (3)	C18—C20—H20A	109.5
C3—C4—H4	119.7	C18—C20—H20B	109.5
C5—C4—H4	119.7	H20A—C20—H20B	109.5
C1—C5—C6	117.8 (3)	C18—C20—H20C	109.5
C1—C5—C4	116.0 (3)	H20A—C20—H20C	109.5
C6—C5—C4	126.2 (3)	H20B—C20—H20C	109.5
C7—C6—C5	117.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O2	0.86	2.23	3.033 (4)	155
N3—H3B···O5i	0.86	2.38	3.161 (4)	151
N6—H6A···O5	0.86	2.11	2.902 (4)	153
N6—H6B···O3ii	0.86	2.18	2.979 (4)	154

Centroid 1	Centroid 2	α	DCC	τ
Cg1	Cg2iii	1.32	3.862 (2)	26.0
Cg2	Cg2iii	0.0	3.823 (2)	24.5

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O2	0.86	2.23	3.033 (4)	155
N3—H3B⋯O5i	0.86	2.38	3.161 (4)	151
N6—H6A⋯O5	0.86	2.11	2.902 (4)	153
N6—H6B⋯O3ii	0.86	2.18	2.979 (4)	154

Symmetry codes: (i) ; (ii) .

Table 2

Main π–π interactions (Å, °)

α is the dihedral angle between the planes. DCC is the length of the CC vector (centroid to centroid). τ is the angle(s) subtended by the plane(s) normal to CC (offset angle). Cg1 is the centroid of ring N1/C1/C5–C8; Cg2 is the centroid of ring N2/C1/C5–C2.

Centroid 1	Centroid 2	α	DCC	τ
Cg1	Cg2iii	1.32	3.862 (2)	26
Cg2	Cg2iii	0.0	3.823 (2)	25

Symmetry code: (iii) .