Tetra-ethyl-ammonium tricarbonyl-chlorido(isoquinoline-1-carboxyl-ato-κN,O)technetate(I).

The asymmetric unit of the title compound, (C(8)H(20)N)[Tc(C(10)H(6)NO(2))Cl(CO)(3)], consists of two crystallographically independent technetium complexes related via a pseudo-inversion centre and two tetra-ethyl-ammonium cations. The Tc atoms have slightly distorted octa-hedral coordination geometries, and they are linked with the cations by inter-molecular C-H⋯O and C-H⋯Cl hydrogen-bonding contacts, forming two-dimensional columns, which lie approximately parallel to (001) in the crystal structure. The isochinolate (isoquinoline-1-carboxyl-ate) ligands link the columns by partial π-π stacking [centroid-centroid distance 4.3733 (11) Å], forming a three-dimensional network structure.

Related literature

For related literature, see: Alberto et al. (1995 ▶, 1996 ▶); Waibel et al. (1999 ▶); Rattat et al. (2001 ▶); Marsh (1995 ▶); Marsh et al. (2002 ▶); Desiraju et al. (1991 ▶); Etter et al. (1990 ▶); Desiraju & Steiner, (1999 ▶); Bernstein et al. (1995 ▶); Steiner & Saenger, 1993 ▶).

Experimental

Crystal data

(C8H20N)[Tc(C10H6NO2)Cl(CO)3]

M = 520.80

Triclinic,

a = 11.7657 (14) Å

b = 12.7481 (14) Å

c = 17.1855 (18) Å

α = 102.878 (12)°

β = 109.624 (12)°

γ = 99.052 (13)°

V = 2290.0 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.78 mm−1

T = 193 (2) K

0.77 × 0.48 × 0.19 mm

Data collection

Stoe IPDS diffractometer

Absorption correction: numerical (Coppens et al., 1965 ▶) T min = 0.670, T max = 0.828

29670 measured reflections

12462 independent reflections

9515 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.067

S = 1.00

12462 reflections

541 parameters

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −1.17 e Å−3

Data collection: IPDS Software (Stoe & Cie, 1997 ▶); cell refinement: IPDS Software; data reduction: X-RED (Stoe & Cie, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON and PLUTON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680802713X/hb2781sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802713X/hb2781Isup2.hkl

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

(C8H20N)[Tc(C10H6NO2)Cl(CO)3]	Z = 4
Mr = 520.80	F000 = 1064
Triclinic, P1	Dx = 1.511 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 11.7657 (14) Å	Cell parameters from 5000 reflections
b = 12.7481 (14) Å	θ = 2.3–30.5º
c = 17.1855 (18) Å	µ = 0.78 mm−1
α = 102.878 (12)º	T = 193 (2) K
β = 109.624 (12)º	Irregular plate, yellow
γ = 99.052 (13)º	0.77 × 0.48 × 0.19 mm
V = 2290.0 (5) Å3

Stoe IPDS diffractometer	12462 independent reflections
Radiation source: fine-focus sealed tube	9515 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.058
T = 193(2) K	θmax = 30.3º
φ rotation scan	θmin = 2.9º
Absorption correction: numerical(Coppens et al., 1965)	h = −16→15
Tmin = 0.670, Tmax = 0.828	k = −17→17
29670 measured reflections	l = −24→24

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)] = 0.028	H-atom parameters constrained
wR(F2) = 0.067	w = 1/[σ2(Fo2) + (0.04P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.003
12462 reflections	Δρmax = 0.54 e Å−3
541 parameters	Δρmin = −1.17 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. Due to the large crystal size a collimator of 0.80 mm diameter was used for the X-ray experiment.

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
Tc1	0.579938 (12)	0.560390 (12)	0.336924 (8)	0.02087 (4)
Tc2	0.915007 (12)	0.971138 (13)	0.672618 (8)	0.02372 (4)
Cl1	0.44939 (4)	0.62682 (4)	0.22082 (3)	0.02909 (9)
Cl2	1.04216 (4)	0.89237 (4)	0.78263 (3)	0.02847 (9)
C11	0.69463 (17)	0.70442 (17)	0.38802 (11)	0.0301 (4)
O11	0.76137 (16)	0.79139 (14)	0.41766 (9)	0.0480 (4)
C21	0.49644 (17)	0.60941 (18)	0.41044 (12)	0.0333 (4)
O21	0.44378 (16)	0.63781 (18)	0.45294 (11)	0.0629 (6)
C31	0.68419 (18)	0.50959 (19)	0.42515 (12)	0.0344 (4)
O31	0.74654 (17)	0.48412 (17)	0.47975 (11)	0.0562 (5)
O41	0.65007 (10)	0.49125 (11)	0.24332 (8)	0.0247 (3)
O51	0.61395 (12)	0.35498 (12)	0.12502 (9)	0.0332 (3)
C41	0.46026 (13)	0.35068 (14)	0.18788 (10)	0.0182 (3)
N51	0.44924 (12)	0.39932 (12)	0.26145 (8)	0.0193 (3)
C61	0.35027 (15)	0.35543 (15)	0.27899 (11)	0.0233 (3)
H61	0.3448	0.3903	0.3321	0.028*
C71	0.25919 (15)	0.26352 (15)	0.22308 (11)	0.0238 (3)
H71	0.1924	0.2344	0.2378	0.029*
C81	0.26467 (14)	0.21165 (15)	0.14299 (10)	0.0215 (3)
C91	0.17206 (16)	0.11541 (17)	0.08350 (12)	0.0299 (4)
H91	0.1046	0.0848	0.0970	0.036*
C101	0.17987 (17)	0.06671 (18)	0.00664 (12)	0.0344 (4)
H101	0.1185	0.0016	−0.0328	0.041*
C111	0.27871 (17)	0.11307 (17)	−0.01395 (12)	0.0313 (4)
H111	0.2810	0.0801	−0.0686	0.038*
C121	0.37207 (16)	0.20468 (16)	0.04271 (10)	0.0252 (4)
H121	0.4389	0.2333	0.0278	0.030*
C131	0.36789 (14)	0.25651 (14)	0.12404 (10)	0.0189 (3)
C141	0.58280 (14)	0.40184 (15)	0.18218 (11)	0.0216 (3)
C12	0.7925 (2)	0.8320 (2)	0.61471 (12)	0.0460 (6)
O12	0.7211 (2)	0.74774 (19)	0.58124 (10)	0.0817 (8)
C22	0.99797 (19)	0.92389 (18)	0.59816 (12)	0.0347 (5)
O22	1.05157 (18)	0.89761 (17)	0.55594 (12)	0.0606 (5)
C32	0.81724 (19)	1.0325 (2)	0.58993 (13)	0.0408 (5)
O32	0.75712 (18)	1.0651 (2)	0.53876 (13)	0.0663 (6)
O42	0.84573 (11)	1.03714 (11)	0.76777 (8)	0.0273 (3)
O52	0.88396 (15)	1.16706 (15)	0.88951 (11)	0.0542 (5)
C42	1.03499 (14)	1.17919 (15)	0.82419 (10)	0.0213 (3)
N52	1.05141 (12)	1.12656 (12)	0.75407 (9)	0.0207 (3)
C62	1.15557 (15)	1.16634 (16)	0.73994 (11)	0.0247 (3)
H62	1.1654	1.1279	0.6894	0.030*
C72	1.24548 (15)	1.25891 (16)	0.79563 (12)	0.0252 (4)
H72	1.3168	1.2841	0.7841	0.030*
C82	1.23181 (15)	1.31745 (15)	0.87097 (11)	0.0233 (3)
C92	1.32207 (17)	1.41574 (17)	0.92933 (12)	0.0312 (4)
H92	1.3939	1.4425	0.9188	0.037*
C102	1.3058 (2)	1.47170 (19)	1.00045 (13)	0.0392 (5)
H102	1.3657	1.5382	1.0390	0.047*
C112	1.2008 (2)	1.4316 (2)	1.01720 (13)	0.0411 (5)
H112	1.1919	1.4708	1.0678	0.049*
C122	1.11075 (18)	1.33701 (18)	0.96199 (12)	0.0332 (4)
H122	1.0401	1.3118	0.9743	0.040*
C132	1.12380 (15)	1.27707 (16)	0.88639 (11)	0.0236 (3)
C142	0.91312 (15)	1.12532 (17)	0.82997 (12)	0.0273 (4)
N1	1.00717 (13)	0.50091 (13)	0.27668 (10)	0.0278 (3)
C151	0.91776 (17)	0.45915 (18)	0.18202 (13)	0.0330 (4)
H15A	0.8319	0.4364	0.1795	0.040*
H15B	0.9214	0.5218	0.1569	0.040*
C161	0.9424 (3)	0.3628 (2)	0.12612 (15)	0.0511 (6)
H16A	0.8807	0.3421	0.0667	0.077*
H16B	0.9363	0.2991	0.1490	0.077*
H16C	1.0263	0.3847	0.1265	0.077*
C171	1.00937 (18)	0.40781 (17)	0.31826 (13)	0.0327 (4)
H17A	1.0720	0.4372	0.3784	0.039*
H17B	1.0372	0.3490	0.2866	0.039*
C181	0.8857 (2)	0.3555 (2)	0.32025 (16)	0.0450 (5)
H18A	0.8958	0.2966	0.3483	0.067*
H18B	0.8233	0.3236	0.2610	0.067*
H18C	0.8580	0.4124	0.3528	0.067*
C191	0.96073 (18)	0.59276 (18)	0.32010 (14)	0.0364 (5)
H19A	0.9631	0.6524	0.2919	0.044*
H19B	0.8725	0.5622	0.3100	0.044*
C201	1.0336 (3)	0.6438 (2)	0.41647 (18)	0.0641 (9)
H20A	0.9978	0.7023	0.4388	0.096*
H20B	1.1208	0.6759	0.4274	0.096*
H20C	1.0293	0.5862	0.4456	0.096*
C211	1.13983 (17)	0.54488 (19)	0.28542 (17)	0.0437 (6)
H21A	1.1955	0.5655	0.3472	0.052*
H21B	1.1649	0.4840	0.2535	0.052*
C221	1.1606 (2)	0.6439 (2)	0.2530 (2)	0.0666 (9)
H22A	1.2485	0.6663	0.2613	0.100*
H22B	1.1386	0.7057	0.2852	0.100*
H22C	1.1082	0.6241	0.1913	0.100*
N2	0.52263 (13)	0.00906 (14)	0.24769 (10)	0.0265 (3)
C152	0.5005 (2)	0.11587 (19)	0.29338 (14)	0.0386 (5)
H15C	0.4839	0.1620	0.2535	0.046*
H15D	0.4246	0.0966	0.3055	0.046*
C162	0.6065 (3)	0.1853 (2)	0.37740 (17)	0.0603 (8)
H16D	0.5838	0.2521	0.4019	0.091*
H16E	0.6818	0.2069	0.3663	0.091*
H16F	0.6222	0.1416	0.4184	0.091*
C172	0.63615 (16)	0.03339 (18)	0.22472 (14)	0.0323 (4)
H17C	0.7094	0.0745	0.2786	0.039*
H17D	0.6522	−0.0382	0.2005	0.039*
C182	0.6258 (2)	0.0996 (2)	0.16093 (17)	0.0437 (5)
H18D	0.7028	0.1110	0.1501	0.065*
H18E	0.6126	0.1719	0.1848	0.065*
H18F	0.5551	0.0589	0.1065	0.065*
C192	0.40524 (17)	−0.0458 (2)	0.16643 (13)	0.0374 (5)
H19C	0.3341	−0.0630	0.1840	0.045*
H19D	0.3891	0.0084	0.1334	0.045*
C202	0.4084 (3)	−0.1512 (2)	0.10697 (16)	0.0547 (7)
H20D	0.3291	−0.1800	0.0568	0.082*
H20E	0.4214	−0.2068	0.1381	0.082*
H20F	0.4768	−0.1352	0.0875	0.082*
C212	0.54784 (19)	−0.06576 (18)	0.30546 (14)	0.0347 (4)
H21C	0.5531	−0.1373	0.2715	0.042*
H21D	0.6301	−0.0308	0.3534	0.042*
C222	0.4516 (3)	−0.0895 (3)	0.34348 (19)	0.0544 (6)
H22D	0.4754	−0.1379	0.3800	0.082*
H22E	0.3701	−0.1267	0.2967	0.082*
H22F	0.4469	−0.0195	0.3785	0.082*

	U11	U22	U33	U12	U13	U23
Tc1	0.01960 (6)	0.02175 (8)	0.01644 (6)	−0.00022 (5)	0.00534 (5)	0.00280 (5)
Tc2	0.02287 (7)	0.02603 (9)	0.01804 (6)	−0.00056 (5)	0.00705 (5)	0.00450 (5)
Cl1	0.0306 (2)	0.0260 (2)	0.02687 (19)	0.00637 (16)	0.00671 (16)	0.00788 (16)
Cl2	0.0301 (2)	0.0237 (2)	0.0297 (2)	0.00575 (15)	0.01008 (16)	0.00745 (17)
C11	0.0328 (9)	0.0322 (11)	0.0183 (7)	−0.0019 (7)	0.0091 (7)	0.0028 (7)
O11	0.0589 (10)	0.0381 (10)	0.0285 (7)	−0.0197 (7)	0.0154 (7)	−0.0010 (6)
C21	0.0300 (9)	0.0352 (12)	0.0264 (8)	−0.0024 (7)	0.0121 (7)	−0.0011 (8)
O21	0.0514 (10)	0.0769 (14)	0.0480 (9)	−0.0003 (9)	0.0319 (8)	−0.0136 (9)
C31	0.0308 (9)	0.0371 (12)	0.0239 (8)	−0.0036 (7)	0.0034 (7)	0.0069 (8)
O31	0.0511 (10)	0.0611 (13)	0.0442 (9)	0.0115 (8)	−0.0011 (8)	0.0246 (9)
O41	0.0192 (5)	0.0235 (7)	0.0287 (6)	0.0003 (4)	0.0115 (5)	0.0028 (5)
O51	0.0310 (6)	0.0288 (8)	0.0399 (7)	0.0010 (5)	0.0240 (6)	−0.0009 (6)
C41	0.0177 (6)	0.0179 (8)	0.0209 (7)	0.0047 (5)	0.0081 (5)	0.0085 (6)
N51	0.0181 (6)	0.0185 (7)	0.0212 (6)	0.0032 (5)	0.0079 (5)	0.0058 (5)
C61	0.0243 (7)	0.0243 (9)	0.0240 (7)	0.0042 (6)	0.0132 (6)	0.0078 (7)
C71	0.0193 (7)	0.0258 (10)	0.0288 (8)	0.0029 (6)	0.0121 (6)	0.0106 (7)
C81	0.0167 (7)	0.0217 (9)	0.0245 (7)	0.0026 (6)	0.0060 (6)	0.0087 (6)
C91	0.0216 (8)	0.0291 (11)	0.0314 (9)	−0.0026 (6)	0.0060 (7)	0.0073 (7)
C101	0.0275 (9)	0.0313 (11)	0.0277 (8)	−0.0028 (7)	0.0004 (7)	−0.0001 (8)
C111	0.0341 (9)	0.0293 (11)	0.0232 (8)	0.0049 (7)	0.0070 (7)	0.0022 (7)
C121	0.0264 (8)	0.0263 (10)	0.0213 (7)	0.0050 (6)	0.0092 (6)	0.0051 (7)
C131	0.0182 (7)	0.0187 (9)	0.0206 (7)	0.0052 (5)	0.0069 (5)	0.0081 (6)
C141	0.0202 (7)	0.0203 (9)	0.0275 (7)	0.0053 (6)	0.0118 (6)	0.0092 (6)
C12	0.0496 (12)	0.0523 (15)	0.0166 (8)	−0.0203 (10)	0.0094 (8)	0.0014 (8)
O12	0.0981 (16)	0.0747 (15)	0.0267 (8)	−0.0562 (12)	0.0153 (9)	−0.0035 (8)
C22	0.0405 (10)	0.0305 (11)	0.0290 (9)	0.0006 (8)	0.0171 (8)	0.0008 (8)
O22	0.0698 (12)	0.0578 (12)	0.0545 (10)	0.0054 (9)	0.0429 (9)	−0.0048 (9)
C32	0.0316 (10)	0.0588 (16)	0.0328 (10)	0.0070 (9)	0.0120 (8)	0.0188 (10)
O32	0.0552 (11)	0.1014 (18)	0.0556 (11)	0.0295 (11)	0.0165 (9)	0.0495 (12)
O42	0.0217 (6)	0.0298 (7)	0.0297 (6)	0.0014 (5)	0.0132 (5)	0.0057 (5)
O52	0.0441 (8)	0.0552 (11)	0.0542 (9)	−0.0112 (7)	0.0374 (8)	−0.0134 (8)
C42	0.0205 (7)	0.0222 (9)	0.0242 (7)	0.0056 (6)	0.0104 (6)	0.0095 (6)
N52	0.0211 (6)	0.0192 (8)	0.0251 (6)	0.0055 (5)	0.0119 (5)	0.0080 (5)
C62	0.0268 (8)	0.0222 (9)	0.0313 (8)	0.0072 (6)	0.0175 (7)	0.0094 (7)
C72	0.0230 (7)	0.0247 (10)	0.0348 (9)	0.0068 (6)	0.0157 (7)	0.0143 (7)
C82	0.0217 (7)	0.0229 (9)	0.0253 (7)	0.0039 (6)	0.0065 (6)	0.0122 (7)
C92	0.0276 (8)	0.0305 (11)	0.0295 (9)	−0.0008 (7)	0.0053 (7)	0.0122 (8)
C102	0.0398 (11)	0.0349 (12)	0.0268 (9)	−0.0066 (8)	0.0038 (8)	0.0037 (8)
C112	0.0482 (12)	0.0400 (13)	0.0254 (9)	−0.0003 (9)	0.0139 (8)	−0.0005 (8)
C122	0.0348 (9)	0.0362 (12)	0.0248 (8)	0.0016 (8)	0.0139 (7)	0.0034 (8)
C132	0.0233 (7)	0.0257 (10)	0.0227 (7)	0.0054 (6)	0.0090 (6)	0.0090 (7)
C142	0.0229 (8)	0.0301 (10)	0.0314 (8)	0.0040 (6)	0.0156 (7)	0.0081 (7)
N1	0.0200 (6)	0.0227 (8)	0.0375 (8)	0.0081 (5)	0.0071 (6)	0.0072 (6)
C151	0.0270 (9)	0.0347 (12)	0.0353 (9)	0.0060 (7)	0.0084 (7)	0.0136 (8)
C161	0.0666 (16)	0.0513 (16)	0.0354 (11)	0.0166 (12)	0.0216 (11)	0.0086 (10)
C171	0.0367 (10)	0.0262 (11)	0.0335 (9)	0.0137 (8)	0.0089 (8)	0.0088 (8)
C181	0.0565 (14)	0.0368 (13)	0.0534 (13)	0.0159 (10)	0.0301 (11)	0.0192 (11)
C191	0.0290 (9)	0.0262 (11)	0.0492 (11)	0.0130 (7)	0.0104 (8)	0.0050 (9)
C201	0.0681 (17)	0.0443 (16)	0.0562 (15)	0.0240 (13)	0.0073 (13)	−0.0114 (13)
C211	0.0189 (8)	0.0355 (12)	0.0734 (15)	0.0099 (7)	0.0139 (9)	0.0137 (11)
C221	0.0342 (12)	0.0507 (17)	0.130 (3)	0.0111 (11)	0.0415 (15)	0.0396 (18)
N2	0.0226 (7)	0.0250 (8)	0.0322 (7)	0.0090 (5)	0.0091 (6)	0.0093 (6)
C152	0.0523 (12)	0.0318 (12)	0.0452 (11)	0.0260 (9)	0.0247 (10)	0.0173 (9)
C162	0.092 (2)	0.0358 (15)	0.0455 (13)	0.0228 (13)	0.0204 (13)	0.0021 (11)
C172	0.0224 (8)	0.0306 (11)	0.0472 (11)	0.0112 (7)	0.0141 (8)	0.0138 (9)
C182	0.0364 (11)	0.0413 (14)	0.0671 (15)	0.0133 (9)	0.0270 (10)	0.0289 (11)
C192	0.0217 (8)	0.0470 (14)	0.0375 (10)	0.0022 (8)	0.0065 (7)	0.0133 (9)
C202	0.0623 (16)	0.0413 (15)	0.0414 (12)	−0.0055 (11)	0.0102 (11)	0.0039 (11)
C212	0.0404 (10)	0.0274 (11)	0.0404 (10)	0.0141 (8)	0.0147 (8)	0.0153 (8)
C222	0.0690 (17)	0.0512 (17)	0.0658 (16)	0.0214 (13)	0.0411 (14)	0.0325 (13)

Tc1—C21	1.9045 (18)	C122—H122	0.9500
Tc1—C31	1.913 (2)	N1—C171	1.515 (3)
Tc1—C11	1.916 (2)	N1—C211	1.517 (2)
Tc1—O41	2.1293 (12)	N1—C191	1.521 (2)
Tc1—N51	2.1778 (15)	N1—C151	1.525 (2)
Tc1—Cl1	2.4822 (6)	C151—C161	1.513 (3)
Tc2—C22	1.9060 (19)	C151—H15A	0.9900
Tc2—C32	1.907 (2)	C151—H15B	0.9900
Tc2—C12	1.913 (2)	C161—H16A	0.9800
Tc2—O42	2.1317 (12)	C161—H16B	0.9800
Tc2—N52	2.1714 (15)	C161—H16C	0.9800
Tc2—Cl2	2.4980 (6)	C171—C181	1.517 (3)
C11—O11	1.145 (2)	C171—H17A	0.9900
C21—O21	1.142 (2)	C171—H17B	0.9900
C31—O31	1.128 (3)	C181—H18A	0.9800
O41—C141	1.286 (2)	C181—H18B	0.9800
O51—C141	1.227 (2)	C181—H18C	0.9800
C41—N51	1.3363 (19)	C191—C201	1.514 (3)
C41—C131	1.424 (2)	C191—H19A	0.9900
C41—C141	1.530 (2)	C191—H19B	0.9900
N51—C61	1.366 (2)	C201—H20A	0.9800
C61—C71	1.362 (2)	C201—H20B	0.9800
C61—H61	0.9500	C201—H20C	0.9800
C71—C81	1.415 (2)	C211—C221	1.508 (4)
C71—H71	0.9500	C211—H21A	0.9900
C81—C91	1.418 (2)	C211—H21B	0.9900
C81—C131	1.428 (2)	C221—H22A	0.9800
C91—C101	1.368 (3)	C221—H22B	0.9800
C91—H91	0.9500	C221—H22C	0.9800
C101—C111	1.407 (3)	N2—C212	1.516 (3)
C101—H101	0.9500	N2—C152	1.520 (3)
C111—C121	1.375 (2)	N2—C192	1.521 (2)
C111—H111	0.9500	N2—C172	1.521 (2)
C121—C131	1.427 (2)	C152—C162	1.515 (3)
C121—H121	0.9500	C152—H15C	0.9900
C12—O12	1.142 (3)	C152—H15D	0.9900
C22—O22	1.141 (2)	C162—H16D	0.9800
C32—O32	1.133 (3)	C162—H16E	0.9800
O42—C142	1.284 (2)	C162—H16F	0.9800
O52—C142	1.224 (2)	C172—C182	1.512 (3)
C42—N52	1.333 (2)	C172—H17C	0.9900
C42—C132	1.427 (2)	C172—H17D	0.9900
C42—C142	1.534 (2)	C182—H18D	0.9800
N52—C62	1.370 (2)	C182—H18E	0.9800
C62—C72	1.361 (2)	C182—H18F	0.9800
C62—H62	0.9500	C192—C202	1.510 (3)
C72—C82	1.416 (2)	C192—H19C	0.9900
C72—H72	0.9500	C192—H19D	0.9900
C82—C92	1.418 (2)	C202—H20D	0.9800
C82—C132	1.425 (2)	C202—H20E	0.9800
C92—C102	1.360 (3)	C202—H20F	0.9800
C92—H92	0.9500	C212—C222	1.509 (3)
C102—C112	1.405 (3)	C212—H21C	0.9900
C102—H102	0.9500	C212—H21D	0.9900
C112—C122	1.375 (3)	C222—H22D	0.9800
C112—H112	0.9500	C222—H22E	0.9800
C122—C132	1.423 (2)	C222—H22F	0.9800
C21—Tc1—C31	89.43 (9)	C211—N1—C191	110.81 (16)
C21—Tc1—C11	87.48 (8)	C171—N1—C151	111.09 (15)
C31—Tc1—C11	89.41 (9)	C211—N1—C151	111.14 (17)
C21—Tc1—O41	172.44 (6)	C191—N1—C151	105.93 (14)
C31—Tc1—O41	94.13 (7)	C161—C151—N1	115.46 (17)
C11—Tc1—O41	99.20 (6)	C161—C151—H15A	108.4
C21—Tc1—N51	98.23 (7)	N1—C151—H15A	108.4
C31—Tc1—N51	96.33 (7)	C161—C151—H15B	108.4
C11—Tc1—N51	171.91 (6)	N1—C151—H15B	108.4
O41—Tc1—N51	74.77 (5)	H15A—C151—H15B	107.5
C21—Tc1—Cl1	92.04 (7)	C151—C161—H16A	109.5
C31—Tc1—Cl1	178.38 (6)	C151—C161—H16B	109.5
C11—Tc1—Cl1	89.97 (6)	H16A—C161—H16B	109.5
O41—Tc1—Cl1	84.49 (4)	C151—C161—H16C	109.5
N51—Tc1—Cl1	84.14 (4)	H16A—C161—H16C	109.5
C22—Tc2—C32	90.02 (10)	H16B—C161—H16C	109.5
C22—Tc2—C12	87.83 (9)	N1—C171—C181	115.07 (17)
C32—Tc2—C12	88.76 (11)	N1—C171—H17A	108.5
C22—Tc2—O42	172.46 (7)	C181—C171—H17A	108.5
C32—Tc2—O42	93.54 (8)	N1—C171—H17B	108.5
C12—Tc2—O42	98.88 (8)	C181—C171—H17B	108.5
C22—Tc2—N52	98.15 (7)	H17A—C171—H17B	107.5
C32—Tc2—N52	96.01 (9)	C171—C181—H18A	109.5
C12—Tc2—N52	172.34 (7)	C171—C181—H18B	109.5
O42—Tc2—N52	74.89 (5)	H18A—C181—H18B	109.5
C22—Tc2—Cl2	90.81 (7)	C171—C181—H18C	109.5
C32—Tc2—Cl2	179.14 (7)	H18A—C181—H18C	109.5
C12—Tc2—Cl2	91.51 (8)	H18B—C181—H18C	109.5
O42—Tc2—Cl2	85.61 (4)	C201—C191—N1	115.09 (17)
N52—Tc2—Cl2	83.64 (4)	C201—C191—H19A	108.5
O11—C11—Tc1	178.6 (2)	N1—C191—H19A	108.5
O21—C21—Tc1	178.41 (18)	C201—C191—H19B	108.5
O31—C31—Tc1	176.9 (2)	N1—C191—H19B	108.5
C141—O41—Tc1	119.02 (10)	H19A—C191—H19B	107.5
N51—C41—C131	121.89 (14)	C191—C201—H20A	109.5
N51—C41—C141	113.66 (13)	C191—C201—H20B	109.5
C131—C41—C141	124.37 (13)	H20A—C201—H20B	109.5
C41—N51—C61	119.94 (14)	C191—C201—H20C	109.5
C41—N51—Tc1	115.46 (11)	H20A—C201—H20C	109.5
C61—N51—Tc1	123.96 (11)	H20B—C201—H20C	109.5
C71—C61—N51	122.38 (15)	C221—C211—N1	115.40 (17)
C71—C61—H61	118.8	C221—C211—H21A	108.4
N51—C61—H61	118.8	N1—C211—H21A	108.4
C61—C71—C81	119.62 (15)	C221—C211—H21B	108.4
C61—C71—H71	120.2	N1—C211—H21B	108.4
C81—C71—H71	120.2	H21A—C211—H21B	107.5
C71—C81—C91	121.18 (15)	C211—C221—H22A	109.5
C71—C81—C131	118.52 (14)	C211—C221—H22B	109.5
C91—C81—C131	120.28 (15)	H22A—C221—H22B	109.5
C101—C91—C81	119.97 (17)	C211—C221—H22C	109.5
C101—C91—H91	120.0	H22A—C221—H22C	109.5
C81—C91—H91	120.0	H22B—C221—H22C	109.5
C91—C101—C111	120.04 (16)	C212—N2—C152	110.98 (15)
C91—C101—H101	120.0	C212—N2—C192	111.54 (16)
C111—C101—H101	120.0	C152—N2—C192	105.92 (15)
C121—C111—C101	121.87 (17)	C212—N2—C172	106.74 (14)
C121—C111—H111	119.1	C152—N2—C172	111.04 (16)
C101—C111—H111	119.1	C192—N2—C172	110.70 (15)
C111—C121—C131	119.52 (16)	C162—C152—N2	115.38 (18)
C111—C121—H121	120.2	C162—C152—H15C	108.4
C131—C121—H121	120.2	N2—C152—H15C	108.4
C41—C131—C121	124.19 (14)	C162—C152—H15D	108.4
C41—C131—C81	117.57 (14)	N2—C152—H15D	108.4
C121—C131—C81	118.25 (14)	H15C—C152—H15D	107.5
O51—C141—O41	124.48 (15)	C152—C162—H16D	109.5
O51—C141—C41	120.41 (15)	C152—C162—H16E	109.5
O41—C141—C41	115.00 (13)	H16D—C162—H16E	109.5
O12—C12—Tc2	178.4 (3)	C152—C162—H16F	109.5
O22—C22—Tc2	177.57 (18)	H16D—C162—H16F	109.5
O32—C32—Tc2	177.4 (2)	H16E—C162—H16F	109.5
C142—O42—Tc2	119.15 (10)	C182—C172—N2	115.37 (15)
N52—C42—C132	121.81 (14)	C182—C172—H17C	108.4
N52—C42—C142	113.73 (14)	N2—C172—H17C	108.4
C132—C42—C142	124.46 (14)	C182—C172—H17D	108.4
C42—N52—C62	120.06 (14)	N2—C172—H17D	108.4
C42—N52—Tc2	116.62 (11)	H17C—C172—H17D	107.5
C62—N52—Tc2	123.11 (11)	C172—C182—H18D	109.5
C72—C62—N52	122.39 (15)	C172—C182—H18E	109.5
C72—C62—H62	118.8	H18D—C182—H18E	109.5
N52—C62—H62	118.8	C172—C182—H18F	109.5
C62—C72—C82	119.44 (15)	H18D—C182—H18F	109.5
C62—C72—H72	120.3	H18E—C182—H18F	109.5
C82—C72—H72	120.3	C202—C192—N2	115.64 (18)
C72—C82—C92	120.99 (16)	C202—C192—H19C	108.4
C72—C82—C132	118.75 (15)	N2—C192—H19C	108.4
C92—C82—C132	120.25 (16)	C202—C192—H19D	108.4
C102—C92—C82	119.95 (18)	N2—C192—H19D	108.4
C102—C92—H92	120.0	H19C—C192—H19D	107.4
C82—C92—H92	120.0	C192—C202—H20D	109.5
C92—C102—C112	120.34 (18)	C192—C202—H20E	109.5
C92—C102—H102	119.8	H20D—C202—H20E	109.5
C112—C102—H102	119.8	C192—C202—H20F	109.5
C122—C112—C102	121.54 (18)	H20D—C202—H20F	109.5
C122—C112—H112	119.2	H20E—C202—H20F	109.5
C102—C112—H112	119.2	C222—C212—N2	114.95 (18)
C112—C122—C132	119.69 (18)	C222—C212—H21C	108.5
C112—C122—H122	120.2	N2—C212—H21C	108.5
C132—C122—H122	120.2	C222—C212—H21D	108.5
C122—C132—C82	118.21 (16)	N2—C212—H21D	108.5
C122—C132—C42	124.23 (16)	H21C—C212—H21D	107.5
C82—C132—C42	117.55 (15)	C212—C222—H22D	109.5
O52—C142—O42	124.11 (16)	C212—C222—H22E	109.5
O52—C142—C42	120.75 (16)	H22D—C222—H22E	109.5
O42—C142—C42	115.12 (14)	C212—C222—H22F	109.5
C171—N1—C211	106.53 (15)	H22D—C222—H22F	109.5
C171—N1—C191	111.44 (16)	H22E—C222—H22F	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C151—H15A···O51	0.99	2.38	3.328 (2)	161
C171—H17A···O31i	0.99	2.50	3.482 (3)	172
C191—H19B···O41	0.99	2.40	3.360 (2)	163
C192—H19C···O42ii	0.99	2.56	3.507 (2)	160
C192—H19C···O52ii	0.99	2.44	3.221 (2)	136
C202—H20E···Cl1iii	0.98	2.81	3.786 (3)	177
C221—H22A···Cl1iv	0.98	2.77	3.652 (2)	151

Table 1

Selected bond lengths (Å)

Tc1—C21	1.9045 (18)
Tc1—C31	1.913 (2)
Tc1—C11	1.916 (2)
Tc1—O41	2.1293 (12)
Tc1—N51	2.1778 (15)
Tc1—Cl1	2.4822 (6)
Tc2—C22	1.9060 (19)
Tc2—C32	1.907 (2)
Tc2—C12	1.913 (2)
Tc2—O42	2.1317 (12)
Tc2—N52	2.1714 (15)
Tc2—Cl2	2.4980 (6)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C151—H15A⋯O51	0.99	2.38	3.328 (2)	161
C171—H17A⋯O31i	0.99	2.50	3.482 (3)	172
C191—H19B⋯O41	0.99	2.40	3.360 (2)	163
C192—H19C⋯O42ii	0.99	2.56	3.507 (2)	160
C192—H19C⋯O52ii	0.99	2.44	3.221 (2)	136
C202—H20E⋯Cl1iii	0.98	2.81	3.786 (3)	177
C221—H22A⋯Cl1iv	0.98	2.77	3.652 (2)	151

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .