Tetra­kis(4-amino-3-methyl­pyridine)diisothio­cyanato­cadmium(II)

In the centrosymmetric title compound, [Cd(NCS)₂(C₆H₈N₂)₄], the Cd^II atom is in a distorted octa­hedral environment. The crystal structure is stabilized by N—H...S hydrogen bonds and weak N—H...π and C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.021
• wR factor = 0.059
• Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    S1     -   C1      ..       7.51 su

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C13
PLAT420_ALERT_2_C D-H Without Acceptor       N3     -   H3B    ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N5     -   H5B    ...          ?

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Tetrakis(4-amino-3-methylpyridine)diisothiocyanatocadmium(II)

Crystal data

[Cd(NCS)2(C6H8N2)4]	F(000) = 1352
Mr = 661.17	Dx = 1.423 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8164 reflections
a = 14.4737 (5) Å	θ = 2.7–26.0°
b = 14.6771 (5) Å	µ = 0.88 mm^−1
c = 15.1822 (6) Å	T = 293 K
β = 106.877 (1)°	Block, colourless
V = 3086.28 (19) Å^3	0.50 × 0.50 × 0.44 mm
Z = 4

Data collection

Siemens SMART CCD area-detector diffractometer	3031 independent reflections
Radiation source: fine-focus sealed tube	2763 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
Detector resolution: 8.33 pixels mm^-1	θmax = 26.0°, θmin = 2.7°
ω scans	h = −17→12
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −18→17
Tmin = 0.652, Tmax = 0.680	l = −17→18
8164 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.059	H-atom parameters constrained
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0292P)^2 + 2.4296P] where P = (Fo^2 + 2Fc^2)/3
3031 reflections	(Δ/σ)max = 0.001
180 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.70 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cd1	0.2500	0.2500	0.5000	0.02744 (7)
S1	0.36739 (5)	0.20629 (6)	0.24490 (4)	0.06429 (18)
N1	0.23500 (13)	0.24769 (11)	0.34049 (12)	0.0407 (4)
N2	0.40290 (10)	0.31961 (10)	0.53144 (10)	0.0335 (3)
N3	0.68691 (13)	0.40289 (18)	0.57047 (16)	0.0749 (7)
H3A	0.7286	0.3950	0.6233	0.090*
H3B	0.7040	0.4278	0.5264	0.090*
N4	0.31984 (10)	0.10376 (10)	0.51741 (10)	0.0341 (3)
N5	0.45553 (14)	−0.14934 (12)	0.53919 (14)	0.0554 (5)
H5A	0.4923	−0.1666	0.5918	0.067*
H5B	0.4469	−0.1842	0.4919	0.067*
C1	0.29006 (14)	0.22989 (13)	0.30109 (12)	0.0348 (4)
C2	0.43163 (13)	0.36017 (12)	0.46424 (12)	0.0343 (4)
H2A	0.3851	0.3696	0.4082	0.041*
C3	0.52419 (13)	0.38882 (12)	0.47157 (13)	0.0360 (4)
C4	0.59429 (13)	0.37611 (13)	0.55674 (14)	0.0417 (4)
C5	0.56504 (13)	0.33539 (14)	0.62767 (14)	0.0432 (4)
H5C	0.6094	0.3264	0.6851	0.052*
C6	0.47082 (13)	0.30873 (13)	0.61223 (12)	0.0369 (4)
H6A	0.4532	0.2817	0.6603	0.044*
C7	0.54929 (17)	0.42876 (16)	0.39078 (15)	0.0527 (5)
H7A	0.4916	0.4360	0.3405	0.079*
H7B	0.5930	0.3888	0.3726	0.079*
H7C	0.5794	0.4871	0.4074	0.079*
C8	0.30708 (13)	0.04799 (12)	0.44468 (12)	0.0352 (4)
H8A	0.2667	0.0681	0.3886	0.042*
C9	0.34898 (13)	−0.03673 (12)	0.44633 (13)	0.0362 (4)
C10	0.41104 (13)	−0.06712 (12)	0.53069 (13)	0.0366 (4)
C11	0.42419 (14)	−0.00973 (13)	0.60665 (13)	0.0408 (4)
H11A	0.4644	−0.0275	0.6637	0.049*
C12	0.37811 (14)	0.07265 (13)	0.59730 (13)	0.0385 (4)
H12A	0.3878	0.1091	0.6493	0.046*
C13	0.32898 (19)	−0.09405 (17)	0.36078 (16)	0.0598 (6)
H13A	0.2853	−0.0622	0.3104	0.090*
H13B	0.3005	−0.1508	0.3707	0.090*
H13C	0.3883	−0.1057	0.3466	0.090*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cd1	0.02303 (10)	0.02906 (11)	0.03032 (11)	0.00019 (6)	0.00788 (7)	−0.00128 (6)
S1	0.0508 (3)	0.0941 (5)	0.0544 (3)	0.0136 (3)	0.0253 (3)	−0.0071 (3)
N1	0.0402 (9)	0.0503 (10)	0.0320 (8)	−0.0015 (7)	0.0111 (7)	−0.0025 (6)
N2	0.0264 (7)	0.0349 (8)	0.0379 (8)	−0.0027 (6)	0.0076 (6)	0.0007 (6)
N3	0.0312 (9)	0.1089 (19)	0.0803 (15)	−0.0153 (11)	0.0096 (9)	0.0309 (13)
N4	0.0323 (7)	0.0304 (7)	0.0395 (8)	0.0022 (6)	0.0102 (6)	−0.0002 (6)
N5	0.0611 (12)	0.0394 (10)	0.0637 (12)	0.0176 (8)	0.0149 (9)	0.0019 (8)
C1	0.0346 (9)	0.0379 (9)	0.0282 (8)	−0.0010 (7)	0.0032 (7)	−0.0009 (7)
C2	0.0347 (9)	0.0313 (9)	0.0344 (9)	−0.0029 (7)	0.0061 (7)	−0.0009 (7)
C3	0.0380 (10)	0.0303 (9)	0.0423 (10)	−0.0026 (7)	0.0160 (8)	−0.0010 (7)
C4	0.0281 (9)	0.0425 (10)	0.0542 (11)	−0.0033 (8)	0.0113 (8)	0.0044 (9)
C5	0.0287 (9)	0.0502 (11)	0.0446 (10)	−0.0022 (8)	0.0012 (8)	0.0080 (9)
C6	0.0320 (9)	0.0408 (10)	0.0371 (9)	−0.0023 (7)	0.0086 (7)	0.0060 (8)
C7	0.0599 (14)	0.0538 (13)	0.0514 (12)	−0.0108 (10)	0.0272 (10)	0.0012 (10)
C8	0.0322 (9)	0.0345 (9)	0.0367 (9)	−0.0001 (7)	0.0065 (7)	0.0011 (7)
C9	0.0345 (9)	0.0327 (9)	0.0429 (10)	−0.0027 (7)	0.0138 (8)	−0.0043 (7)
C10	0.0319 (9)	0.0308 (9)	0.0503 (10)	0.0026 (7)	0.0170 (8)	0.0036 (8)
C11	0.0392 (10)	0.0412 (10)	0.0386 (9)	0.0042 (8)	0.0062 (8)	0.0063 (8)
C12	0.0422 (10)	0.0362 (10)	0.0364 (9)	0.0007 (8)	0.0101 (8)	−0.0039 (7)
C13	0.0693 (15)	0.0518 (13)	0.0549 (13)	0.0048 (11)	0.0124 (11)	−0.0168 (11)

Geometric parameters (Å, º)

Cd1—N4	2.3545 (14)	C3—C4	1.405 (3)
Cd1—N4^i	2.3545 (14)	C3—C7	1.496 (3)
Cd1—N2^i	2.3571 (14)	C4—C5	1.400 (3)
Cd1—N2	2.3571 (14)	C5—C6	1.372 (2)
Cd1—N1^i	2.3681 (17)	C5—H5C	0.93
Cd1—N1	2.3681 (17)	C6—H6A	0.93
S1—C1	1.629 (2)	C7—H7A	0.96
N1—C1	1.157 (3)	C7—H7B	0.96
N2—C6	1.340 (2)	C7—H7C	0.96
N2—C2	1.347 (2)	C8—C9	1.380 (3)
N3—C4	1.354 (2)	C8—H8A	0.93
N3—H3A	0.86	C9—C10	1.407 (3)
N3—H3B	0.86	C9—C13	1.503 (3)
N4—C12	1.340 (2)	C10—C11	1.396 (3)
N4—C8	1.344 (2)	C11—C12	1.368 (3)
N5—C10	1.356 (2)	C11—H11A	0.93
N5—H5A	0.86	C12—H12A	0.93
N5—H5B	0.86	C13—H13A	0.96
C2—C3	1.377 (2)	C13—H13B	0.96
C2—H2A	0.93	C13—H13C	0.96
N4—Cd1—N4^i	180.0	N3—C4—C3	121.42 (19)
N4—Cd1—N2^i	88.56 (5)	C5—C4—C3	117.75 (16)
N4^i—Cd1—N2^i	91.44 (5)	C6—C5—C4	119.85 (17)
N4—Cd1—N2	91.44 (5)	C6—C5—H5C	120.1
N4^i—Cd1—N2	88.56 (5)	C4—C5—H5C	120.1
N2^i—Cd1—N2	180.0	N2—C6—C5	123.43 (17)
N4—Cd1—N1^i	89.39 (5)	N2—C6—H6A	118.3
N4^i—Cd1—N1^i	90.61 (5)	C5—C6—H6A	118.3
N2^i—Cd1—N1^i	90.87 (6)	C3—C7—H7A	109.5
N2—Cd1—N1^i	89.13 (6)	C3—C7—H7B	109.5
N4—Cd1—N1	90.61 (5)	H7A—C7—H7B	109.5
N4^i—Cd1—N1	89.39 (5)	C3—C7—H7C	109.5
N2^i—Cd1—N1	89.13 (6)	H7A—C7—H7C	109.5
N2—Cd1—N1	90.87 (6)	H7B—C7—H7C	109.5
N1^i—Cd1—N1	180.0	N4—C8—C9	125.38 (17)
C1—N1—Cd1	131.28 (15)	N4—C8—H8A	117.3
C6—N2—C2	116.11 (15)	C9—C8—H8A	117.3
C6—N2—Cd1	121.98 (12)	C8—C9—C10	117.59 (16)
C2—N2—Cd1	121.09 (11)	C8—C9—C13	121.00 (18)
C4—N3—H3A	120.0	C10—C9—C13	121.41 (17)
C4—N3—H3B	120.0	N5—C10—C11	120.75 (18)
H3A—N3—H3B	120.0	N5—C10—C9	121.93 (18)
C12—N4—C8	115.88 (15)	C11—C10—C9	117.31 (16)
C12—N4—Cd1	123.29 (12)	C12—C11—C10	120.14 (17)
C8—N4—Cd1	120.73 (11)	C12—C11—H11A	119.9
C10—N5—H5A	120.0	C10—C11—H11A	119.9
C10—N5—H5B	120.0	N4—C12—C11	123.68 (17)
H5A—N5—H5B	120.0	N4—C12—H12A	118.2
N1—C1—S1	179.16 (19)	C11—C12—H12A	118.2
N2—C2—C3	125.49 (16)	C9—C13—H13A	109.5
N2—C2—H2A	117.3	C9—C13—H13B	109.5
C3—C2—H2A	117.3	H13A—C13—H13B	109.5
C2—C3—C4	117.34 (17)	C9—C13—H13C	109.5
C2—C3—C7	121.02 (17)	H13A—C13—H13C	109.5
C4—C3—C7	121.60 (17)	H13B—C13—H13C	109.5
N3—C4—C5	120.82 (19)
N4—Cd1—N1—C1	−49.03 (19)	N2—C2—C3—C7	176.74 (18)
N4^i—Cd1—N1—C1	130.97 (19)	C2—C3—C4—N3	−179.4 (2)
N2^i—Cd1—N1—C1	−137.58 (19)	C7—C3—C4—N3	2.7 (3)
N2—Cd1—N1—C1	42.42 (19)	C2—C3—C4—C5	0.0 (3)
N4—Cd1—N2—C6	−61.72 (14)	C7—C3—C4—C5	−177.85 (19)
N4^i—Cd1—N2—C6	118.28 (14)	N3—C4—C5—C6	−180.0 (2)
N1^i—Cd1—N2—C6	27.64 (14)	C3—C4—C5—C6	0.6 (3)
N1—Cd1—N2—C6	−152.36 (14)	C2—N2—C6—C5	−0.8 (3)
N4—Cd1—N2—C2	107.54 (14)	Cd1—N2—C6—C5	168.92 (15)
N4^i—Cd1—N2—C2	−72.46 (14)	C4—C5—C6—N2	−0.2 (3)
N1^i—Cd1—N2—C2	−163.09 (14)	C12—N4—C8—C9	−0.3 (3)
N1—Cd1—N2—C2	16.91 (14)	Cd1—N4—C8—C9	176.22 (14)
N2^i—Cd1—N4—C12	−115.25 (15)	N4—C8—C9—C10	−0.7 (3)
N2—Cd1—N4—C12	64.75 (15)	N4—C8—C9—C13	179.44 (19)
N1^i—Cd1—N4—C12	−24.37 (15)	C8—C9—C10—N5	179.97 (18)
N1—Cd1—N4—C12	155.63 (15)	C13—C9—C10—N5	−0.2 (3)
N2^i—Cd1—N4—C8	68.52 (13)	C8—C9—C10—C11	1.0 (3)
N2—Cd1—N4—C8	−111.48 (13)	C13—C9—C10—C11	−179.1 (2)
N1^i—Cd1—N4—C8	159.41 (14)	N5—C10—C11—C12	−179.35 (19)
N1—Cd1—N4—C8	−20.59 (14)	C9—C10—C11—C12	−0.4 (3)
C6—N2—C2—C3	1.5 (3)	C8—N4—C12—C11	1.0 (3)
Cd1—N2—C2—C3	−168.32 (14)	Cd1—N4—C12—C11	−175.41 (14)
N2—C2—C3—C4	−1.1 (3)	C10—C11—C12—N4	−0.7 (3)

Symmetry code: (i) −x+1/2, −y+1/2, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···S1^ii	0.86	2.74	3.520 (2)	152
N5—H5A···S1^iii	0.86	2.77	3.624 (2)	171
N3—H3B···Cg2^iv	0.86	2.69	3.328 (2)	132
N5—H5B···Cg1^iii	0.86	2.64	3.324 (2)	137
C7—H7C···Cg1^v	0.96	2.85	3.545 (2)	130

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