(N,N,N′,N′′,N′′-Penta­methyl­diethylenetriamine-κ³N,N′,N′′)(trithio­cyanurato-κ²N,S)zinc(II)

The structure of the title compound, [Zn(C₉H₂₃N₃)(C₃HN₃S₃)], consists of discrete mol­ecules connected by N—H...S hydrogen bonds into centrosymmetric dimers. The Zn^II atom is penta­coordinated in a deformed trigonal–bipyramidal geometry by three N atoms of a tridentate N,N,N′,N′′,N′′-penta­methyl­diethylenetriamine ligand, and one S and one N atoms of a trithio­cyanurate dianion bonded as a bidentate ligand. The crystal structure is further stabilized by close contacts of the types C—H...S and C—H...N.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.046
• wR factor = 0.117
• Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.767     1.000
            Tmin(prime) and Tmax expected:      0.489     0.546
            RR(prime) =      0.856
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.83
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.55
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.22
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7A    ..  S2      ..       2.95 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10C   ..  S1      ..       3.00 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8C    ..  N3      ..       2.74 Ang.

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.546
            Tmax scaled      0.546 Tmin scaled      0.418

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED (Oxford Diffraction, 2002); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97 and DIAMOND.

(N,N,N',N'',N''-Pentamethyldiethylenetriamine-κ³N,N',N'')(trithiocyanurato- κ²N,S)zinc(II)

Crystal data

[Zn(C9H23N3)(C3HN3S3)]	F(000) = 864
Mr = 413.92	Dx = 1.540 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4190 reflections
a = 12.6748 (10) Å	θ = 2.6–30.3°
b = 9.3292 (7) Å	µ = 1.73 mm^−1
c = 16.2528 (17) Å	T = 100 K
β = 111.694 (10)°	Prism, light yellow
V = 1785.7 (3) Å^3	0.40 × 0.40 × 0.35 mm
Z = 4

Data collection

Oxford Diffraction Xcalibur2 CCD area-detector diffractometer	3134 independent reflections
Radiation source: fine-focus sealed tube	2977 reflections with I > 2σ(I)
Enhance (Oxford Diffraction) monochromator	Rint = 0.045
Detector resolution: 16.3 pixels mm^-1	θmax = 25.0°, θmin = 3.5°
rotation method, ω scans	h = −15→14
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2002)	k = −11→10
Tmin = 0.767, Tmax = 1.000	l = −19→18
7920 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.118	H-atom parameters constrained
S = 1.20	w = 1/[σ^2(Fo^2) + (0.0275P)^2 + 1P] where P = (Fo^2 + 2Fc^2)/3
3134 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 1.31 e Å^−3
0 restraints	Δρmin = −0.41 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
Zn1	0.47902 (4)	0.64484 (5)	0.71278 (3)	0.01188 (16)
S1	0.11911 (9)	0.61235 (11)	0.60813 (7)	0.0143 (2)
N1	0.3246 (3)	0.5314 (4)	0.6134 (2)	0.0131 (7)
C1	0.2117 (4)	0.5181 (4)	0.5756 (3)	0.0122 (8)
S2	0.17556 (10)	0.23763 (12)	0.38569 (7)	0.0196 (3)
C2	0.2377 (4)	0.3382 (4)	0.4773 (3)	0.0139 (9)
N2	0.1693 (3)	0.4223 (4)	0.5066 (2)	0.0129 (7)
H2A	0.0952	0.4145	0.4800	0.015*
S3	0.53436 (9)	0.45138 (12)	0.64683 (7)	0.0190 (3)
N3	0.3512 (3)	0.3396 (4)	0.5227 (2)	0.0166 (8)
C3	0.3899 (4)	0.4363 (5)	0.5874 (3)	0.0143 (9)
N4	0.4565 (3)	0.8466 (4)	0.6498 (2)	0.0158 (8)
C4	0.5330 (4)	0.9496 (5)	0.7139 (3)	0.0196 (10)
H4A	0.4975	0.9811	0.7559	0.024*
H4B	0.5434	1.0352	0.6817	0.024*
N5	0.6350 (3)	0.7442 (4)	0.8051 (2)	0.0151 (8)
C5	0.6479 (4)	0.8833 (5)	0.7652 (3)	0.0178 (9)
H5A	0.6894	0.8680	0.7249	0.021*
H5B	0.6930	0.9498	0.8126	0.021*
N6	0.4394 (3)	0.6118 (4)	0.8253 (2)	0.0135 (7)
C6	0.6097 (4)	0.7654 (5)	0.8863 (3)	0.0170 (9)
H6A	0.5624	0.8522	0.8797	0.020*
H6B	0.6815	0.7797	0.9376	0.020*
C7	0.5476 (4)	0.6362 (5)	0.9025 (3)	0.0172 (9)
H7A	0.5965	0.5503	0.9120	0.021*
H7B	0.5306	0.6519	0.9566	0.021*
C8	0.4912 (5)	0.8248 (6)	0.5726 (3)	0.0281 (11)
H8A	0.4829	0.9149	0.5399	0.042*
H8B	0.4430	0.7512	0.5336	0.042*
H8C	0.5707	0.7937	0.5936	0.042*
C9	0.3398 (4)	0.9029 (5)	0.6183 (3)	0.0239 (10)
H9A	0.3375	0.9963	0.5900	0.036*
H9B	0.3154	0.9138	0.6685	0.036*
H9C	0.2889	0.8361	0.5752	0.036*
C10	0.3491 (4)	0.7094 (5)	0.8289 (3)	0.0178 (9)
H10A	0.3335	0.6898	0.8826	0.027*
H10B	0.2799	0.6939	0.7767	0.027*
H10C	0.3741	0.8090	0.8298	0.027*
C11	0.4013 (4)	0.4624 (5)	0.8262 (3)	0.0174 (9)
H11A	0.3828	0.4468	0.8790	0.026*
H11B	0.4621	0.3966	0.8273	0.026*
H11C	0.3338	0.4445	0.7730	0.026*
C12	0.7380 (4)	0.6570 (5)	0.8237 (3)	0.0183 (9)
H12A	0.8035	0.7083	0.8652	0.027*
H12B	0.7501	0.6390	0.7685	0.027*
H12C	0.7288	0.5654	0.8500	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0146 (3)	0.0096 (3)	0.0104 (3)	−0.00098 (18)	0.0034 (2)	−0.00234 (18)
S1	0.0151 (5)	0.0117 (5)	0.0150 (5)	0.0011 (4)	0.0043 (4)	−0.0032 (4)
N1	0.0157 (19)	0.0082 (17)	0.0123 (17)	0.0003 (14)	0.0017 (14)	−0.0012 (14)
C1	0.019 (2)	0.0065 (19)	0.0103 (19)	−0.0004 (16)	0.0048 (17)	0.0020 (16)
S2	0.0198 (6)	0.0192 (6)	0.0190 (6)	−0.0056 (5)	0.0061 (5)	−0.0110 (5)
C2	0.019 (2)	0.008 (2)	0.015 (2)	−0.0020 (17)	0.0078 (18)	0.0005 (17)
N2	0.0139 (18)	0.0100 (17)	0.0115 (17)	−0.0017 (14)	0.0010 (14)	−0.0013 (14)
S3	0.0131 (5)	0.0195 (6)	0.0209 (6)	0.0021 (4)	0.0022 (4)	−0.0093 (5)
N3	0.0170 (19)	0.0139 (19)	0.0175 (19)	−0.0011 (15)	0.0047 (16)	−0.0041 (15)
C3	0.016 (2)	0.012 (2)	0.013 (2)	0.0011 (17)	0.0042 (17)	−0.0014 (17)
N4	0.0164 (19)	0.0165 (19)	0.0144 (18)	−0.0028 (15)	0.0057 (15)	0.0005 (15)
C4	0.019 (2)	0.016 (2)	0.023 (2)	−0.0025 (18)	0.0062 (19)	0.0015 (19)
N5	0.0155 (18)	0.0123 (18)	0.0173 (18)	0.0001 (15)	0.0058 (15)	−0.0008 (15)
C5	0.020 (2)	0.011 (2)	0.020 (2)	−0.0040 (18)	0.0044 (19)	−0.0006 (18)
N6	0.0173 (19)	0.0094 (17)	0.0119 (17)	−0.0023 (14)	0.0033 (15)	−0.0018 (14)
C6	0.016 (2)	0.018 (2)	0.013 (2)	−0.0039 (18)	0.0019 (17)	−0.0056 (18)
C7	0.019 (2)	0.017 (2)	0.011 (2)	−0.0011 (18)	0.0002 (17)	−0.0004 (17)
C8	0.037 (3)	0.033 (3)	0.017 (2)	0.001 (2)	0.013 (2)	0.004 (2)
C9	0.020 (2)	0.020 (2)	0.031 (3)	0.0022 (19)	0.007 (2)	0.006 (2)
C10	0.021 (2)	0.016 (2)	0.018 (2)	0.0012 (19)	0.0083 (19)	−0.0024 (18)
C11	0.022 (2)	0.011 (2)	0.018 (2)	−0.0020 (17)	0.0057 (18)	0.0019 (17)
C12	0.016 (2)	0.015 (2)	0.022 (2)	0.0023 (18)	0.0034 (18)	0.0016 (18)

Geometric parameters (Å, º)

Zn1—N6	2.091 (4)	C5—H5B	0.9900
Zn1—N4	2.111 (4)	N6—C11	1.478 (5)
Zn1—N5	2.197 (4)	N6—C10	1.480 (6)
Zn1—N1	2.286 (4)	N6—C7	1.495 (5)
Zn1—S3	2.3354 (12)	C6—C7	1.515 (6)
S1—C1	1.700 (4)	C6—H6A	0.9900
N1—C1	1.338 (6)	C6—H6B	0.9900
N1—C3	1.381 (6)	C7—H7A	0.9900
C1—N2	1.378 (5)	C7—H7B	0.9900
S2—C2	1.688 (4)	C8—H8A	0.9800
C2—N3	1.352 (6)	C8—H8B	0.9800
C2—N2	1.379 (6)	C8—H8C	0.9800
N2—H2A	0.8800	C9—H9A	0.9800
S3—C3	1.732 (4)	C9—H9B	0.9800
N3—C3	1.333 (6)	C9—H9C	0.9800
N4—C9	1.471 (6)	C10—H10A	0.9800
N4—C4	1.485 (6)	C10—H10B	0.9800
N4—C8	1.488 (6)	C10—H10C	0.9800
C4—C5	1.517 (6)	C11—H11A	0.9800
C4—H4A	0.9900	C11—H11B	0.9800
C4—H4B	0.9900	C11—H11C	0.9800
N5—C12	1.471 (6)	C12—H12A	0.9800
N5—C6	1.482 (5)	C12—H12B	0.9800
N5—C5	1.487 (6)	C12—H12C	0.9800
C5—H5A	0.9900
N6—Zn1—N4	121.50 (14)	H5A—C5—H5B	108.0
N6—Zn1—N5	84.93 (14)	C11—N6—C10	108.7 (3)
N4—Zn1—N5	83.19 (14)	C11—N6—C7	109.7 (3)
N6—Zn1—N1	97.48 (13)	C10—N6—C7	110.9 (3)
N4—Zn1—N1	98.23 (13)	C11—N6—Zn1	109.4 (3)
N5—Zn1—N1	175.95 (13)	C10—N6—Zn1	112.5 (3)
N6—Zn1—S3	119.86 (10)	C7—N6—Zn1	105.6 (3)
N4—Zn1—S3	118.42 (11)	N5—C6—C7	110.3 (4)
N5—Zn1—S3	106.98 (10)	N5—C6—H6A	109.6
N1—Zn1—S3	69.00 (9)	C7—C6—H6A	109.6
C1—N1—C3	117.4 (4)	N5—C6—H6B	109.6
C1—N1—Zn1	149.1 (3)	C7—C6—H6B	109.6
C3—N1—Zn1	93.4 (3)	H6A—C6—H6B	108.1
N1—C1—N2	117.6 (4)	N6—C7—C6	110.5 (3)
N1—C1—S1	123.6 (3)	N6—C7—H7A	109.6
N2—C1—S1	118.8 (3)	C6—C7—H7A	109.6
N3—C2—N2	118.9 (4)	N6—C7—H7B	109.6
N3—C2—S2	122.9 (3)	C6—C7—H7B	109.6
N2—C2—S2	118.2 (3)	H7A—C7—H7B	108.1
C1—N2—C2	123.0 (4)	N4—C8—H8A	109.5
C1—N2—H2A	118.5	N4—C8—H8B	109.5
C2—N2—H2A	118.5	H8A—C8—H8B	109.5
C3—S3—Zn1	83.32 (15)	N4—C8—H8C	109.5
C3—N3—C2	116.4 (4)	H8A—C8—H8C	109.5
N3—C3—N1	126.0 (4)	H8B—C8—H8C	109.5
N3—C3—S3	120.0 (3)	N4—C9—H9A	109.5
N1—C3—S3	114.0 (3)	N4—C9—H9B	109.5
C9—N4—C4	108.9 (4)	H9A—C9—H9B	109.5
C9—N4—C8	109.1 (4)	N4—C9—H9C	109.5
C4—N4—C8	111.1 (4)	H9A—C9—H9C	109.5
C9—N4—Zn1	115.2 (3)	H9B—C9—H9C	109.5
C4—N4—Zn1	107.5 (3)	N6—C10—H10A	109.5
C8—N4—Zn1	104.9 (3)	N6—C10—H10B	109.5
N4—C4—C5	111.5 (4)	H10A—C10—H10B	109.5
N4—C4—H4A	109.3	N6—C10—H10C	109.5
C5—C4—H4A	109.3	H10A—C10—H10C	109.5
N4—C4—H4B	109.3	H10B—C10—H10C	109.5
C5—C4—H4B	109.3	N6—C11—H11A	109.5
H4A—C4—H4B	108.0	N6—C11—H11B	109.5
C12—N5—C6	110.9 (3)	H11A—C11—H11B	109.5
C12—N5—C5	109.9 (3)	N6—C11—H11C	109.5
C6—N5—C5	111.5 (3)	H11A—C11—H11C	109.5
C12—N5—Zn1	114.4 (3)	H11B—C11—H11C	109.5
C6—N5—Zn1	103.2 (3)	N5—C12—H12A	109.5
C5—N5—Zn1	106.7 (3)	N5—C12—H12B	109.5
N5—C5—C4	111.0 (4)	H12A—C12—H12B	109.5
N5—C5—H5A	109.4	N5—C12—H12C	109.5
C4—C5—H5A	109.4	H12A—C12—H12C	109.5
N5—C5—H5B	109.4	H12B—C12—H12C	109.5
C4—C5—H5B	109.4

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···S1^i	0.88	2.57	3.450 (4)	176
C7—H7A···S2^ii	0.99	2.95	3.899 (5)	160
C11—H11B···S2^ii	0.98	2.81	3.744 (5)	160
C10—H10C···S1^iii	0.98	3.00	3.878 (5)	150
C8—H8C···N3^iv	0.98	2.74	3.321 (6)	119

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x+1/2, −y+1/2, z+1/2; (iii) −x+1/2, y+1/2, −z+3/2; (iv) −x+1, −y+1, −z+1.