(p-Methyl­benzene­thiol­ato)[tris(3-phenyl-5-methyl­pyrazol­yl)­borato]zinc(II)

Görls, H.; Günther, W.; Notni, J.; Anders, E.

doi:10.1107/S160053680704439X

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(p-Methylbenzenethiolato)[tris(3-phenyl-5-methylpyrazolyl)borato]zinc(II)

H. Görls, W. Günther, J. Notni and E. Anders

The crystal structure of the title compound, [Zn(C₃₀H₂₈BN₆)(C₇H₇S)], is closely related to a series of other tripod zinc thiolates. The Zn atom adopts a very distorted tetrahedral coordination geometry. In addition to the crystallographic data, ¹¹B NMR as well as ¹¹B-decoupled ¹H NMR data are provided. A proton shift for the boron-bound hydride (5.15 p.p.m.) of a pyrazolylborato ligand is reported for the first time.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680704439X/bt2507sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680704439X/bt2507Isup2.hkl Contains datablock I

CCDC reference: 663606

checkCIF report

Key indicators

Single-crystal X-ray study
T = 183 K
Mean (C-C) = 0.004 Å
R factor = 0.038
wR factor = 0.087
Data-to-parameter ratio = 18.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.12 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.36 Ratio
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C31
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1

Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
           From the CIF: _diffrn_reflns_theta_max           27.48
           From the CIF: _reflns_number_total               7635
           From the CIF: _diffrn_reflns_limit_ max hkl   21.   13.   22.
           From the CIF: _diffrn_reflns_limit_ min hkl  -21.  -14.  -22.
           TEST1: Expected hkl limits for theta max
           Calculated maximum hkl   21.   16.   22.
           Calculated minimum hkl  -21.  -16.  -22.
PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn          (2)       1.88

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

   1 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
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

The title compound is closely related to a class of complexes synthesized by Tekeste and Vahrenkamp (2006), which are useful model compounds for thiolate alkylating enzymes. Thus, their structural chemistry and reactivity has been extensively studied by these authors. However, to the best of our knowledge, no comment on the chemical shift of the single hydride ion at the boron atom can be found in the literature. In routine ¹H spectra, this signal is usually not detected due to ¹¹B-¹H coupling: Natural boron isotopes are ¹⁰B (19.9%, spin 3/2) and ¹¹B (80.1%, spin 3), both of them possessing large quadrupol moments. This causes the signal of the hydride to exhibit a large multiplicity and increased band width. As a result, the detected signal appears in the spectra as a slight elevation of the baseline, which normally is not considered a real peak by most processing software. Nonetheless, in a ¹¹B decoupled ¹H NMR, a slightly broadened singlet at 5.15 p.p.m. with a relative intensity of 0.8 protons is found which corresponds to the hydride. The unusual intensity is a result of the natural abundance of the ¹¹B nucleus of ~80%, since only this portion of the signal experiences line width reduction by decoupling. The moleculare structure of (1) is shown in Fig. 1. The Zn atom is coordinated by three N atoms and one sulfur atom in a distorted tetrahedral arrangement. The Zn–S bond length is 2.2289 (6) Å and the Zn—N bond lengths are 2.038 (2), 2.058 (2) and 2.088 (2) Å, respectively. The bond angles around Zn range from 120.98 (5) to 127.46 (5)° for S–Zn–N angles and from 91.59 (7) to 94.66 (7)° for N–Zn–N angles. The Zn–N and Zn–S distances are in agreement with the corresponding distances in the other Zn complexes reported in the literature (Rombach et al., 2002; Börzel et al., 2003; Brand et al., 2001). There are no unexpected geometrical features associated with the coordination structure of zinc.

Related literature top

Tris(pyrazolyl)borato zinc thiolates and their reactions have been studied by Brand et al. (2001). A comparative kinetic study on thiolate alkylation in tripodal zinc complexes with N₃S, N₂S₂, NS₃ and S₄ donor sets has been published by Tekeste & Vahrenkamp (2006).

For related literature, see: Börzel et al. (2003); Rombach et al. (2002).

Experimental top

To a solution of Tp^(Ph,Me)ZnOH (1 mmol, 561 mg) in methylene chloride (20 ml) 4-methylthiophenol (1 mmol, 124 mg) were added. The mixture was stirred for 1 h, and methanol (10 ml) was added. The methylene chloride was evaporated, and the complex was allowed to precipitate at -20 °C. Obtained were colourless prisms, m. p. 230 °C, yield 640 mg (95%). Anal. calcd. for C₃₇H₃₅BN₆SZn: C, 66.14, H, 5.25, N, 12.50, S, 4.77. Found C, 66.74, H, 5.02, N, 12.69, S, 4.89. NMR (¹H, 400 MHz, CDCl₃,¹¹B-decoupled): 1.95 (s, 3H), 2.55 (s, 9H), 5.15 (s, 0.8H) 6.12 (d, 2H), 6.26 (d, 2H), 7.11 (m, 9H), 7.59 (m, 6H) p.p.m.. NMR (¹¹B, 128.4 MHz, CDCl₃): -6.3 p.p.m.. NMR (¹³C, 100 MHz, CDCl₃): 12.9, 20.5, 105.5, 127.5, 127.8, 128.1, 128.5, 129.7, 131.0, 131.2, 136.9, 145.7, 154.5 p.p.m..

Structure description top

For related literature, see: Börzel et al. (2003); Rombach et al. (2002).

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Siemens, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 40% probability level.

(p-Methylbenzenethiolato)[tris(3-phenyl-5-methylpyrazolyl)borato]zinc(II) top

Crystal data top

[Zn(C₃₀H₂₈BN₆)(C₇H₇S)]	Z = 4
M_r = 671.95	F(000) = 1400
Monoclinic, P2₁/n	D_x = 1.306 Mg m⁻³
Hall symbol: -P2yn	Mo Kα radiation, λ = 0.71073 Å
a = 16.2448 (7) Å	µ = 0.82 mm⁻¹
b = 12.3442 (3) Å	T = 183 K
c = 17.3988 (7) Å	Prism, colourless
β = 101.675 (1)°	0.18 × 0.12 × 0.10 mm
V = 3416.8 (2) Å³

Data collection top

Nonius KappaCCD diffractometer	4579 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.040
Graphite monochromator	θ_max = 27.5°, θ_min = 2.5°
phi– + ω–scan	h = −21→21
13913 measured reflections	k = −14→13
7635 independent reflections	l = −22→22

Refinement top

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 0.87	w = 1/[σ²(F_o²) + (0.0428P)²] where P = (F_o² + 2F_c²)/3
7635 reflections	(Δ/σ)_max = 0.001
422 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

[Zn(C₃₀H₂₈BN₆)(C₇H₇S)]	V = 3416.8 (2) Å³
M_r = 671.95	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 16.2448 (7) Å	µ = 0.82 mm⁻¹
b = 12.3442 (3) Å	T = 183 K
c = 17.3988 (7) Å	0.18 × 0.12 × 0.10 mm
β = 101.675 (1)°

Data collection top

Nonius KappaCCD diffractometer	4579 reflections with I > 2σ(I)
13913 measured reflections	R_int = 0.040
7635 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 0.87	Δρ_max = 0.43 e Å⁻³
7635 reflections	Δρ_min = −0.41 e Å⁻³
422 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Zn	0.829763 (16)	0.72798 (2)	0.034357 (14)	0.03008 (9)
S	0.70537 (4)	0.66651 (5)	−0.02881 (3)	0.03546 (15)
N1	0.93538 (11)	0.70497 (13)	−0.00994 (11)	0.0314 (4)
N2	1.00753 (11)	0.72512 (14)	0.04482 (10)	0.0325 (4)
N3	0.88773 (11)	0.66740 (14)	0.14189 (10)	0.0306 (4)
N4	0.95800 (11)	0.72717 (13)	0.17318 (10)	0.0297 (4)
N5	0.86364 (11)	0.88850 (13)	0.06250 (10)	0.0315 (4)
N6	0.94927 (11)	0.89614 (13)	0.09183 (10)	0.0312 (4)
C1	0.64030 (15)	0.68671 (18)	0.04035 (14)	0.0368 (6)
C2	0.66207 (16)	0.75162 (19)	0.10691 (14)	0.0440 (6)
H2A	0.7139	0.7898	0.1160	0.053*
C3	0.60969 (19)	0.7614 (2)	0.15993 (16)	0.0540 (7)
H3A	0.6266	0.8056	0.2051	0.065*
C4	0.53267 (19)	0.7081 (2)	0.14872 (18)	0.0581 (8)
C5	0.51059 (17)	0.6458 (2)	0.0817 (2)	0.0581 (8)
H5A	0.4580	0.6095	0.0720	0.070*
C6	0.56291 (15)	0.63468 (19)	0.02811 (16)	0.0467 (7)
H6A	0.5456	0.5911	−0.0173	0.056*
C7	0.4756 (2)	0.7200 (3)	0.2067 (2)	0.0938 (12)
H7A	0.5088	0.7145	0.2602	0.141*
H7B	0.4331	0.6625	0.1979	0.141*
H7C	0.4477	0.7907	0.1996	0.141*
C8	0.95876 (15)	0.64799 (17)	−0.06788 (13)	0.0343 (5)
C9	1.04514 (15)	0.63145 (18)	−0.05002 (14)	0.0402 (6)
H9A	1.0777	0.5938	−0.0811	0.048*
C10	1.07439 (15)	0.68013 (18)	0.02127 (14)	0.0364 (6)
C11	1.16243 (15)	0.6886 (2)	0.06763 (15)	0.0476 (7)
H11A	1.1651	0.6586	0.1202	0.071*
H11B	1.1795	0.7648	0.0719	0.071*
H11C	1.2003	0.6478	0.0411	0.071*
C12	0.89822 (15)	0.61680 (17)	−0.13931 (13)	0.0348 (6)
C13	0.82745 (15)	0.6780 (2)	−0.16843 (14)	0.0416 (6)
H13A	0.8155	0.7398	−0.1401	0.050*
C14	0.77392 (17)	0.6506 (2)	−0.23795 (15)	0.0544 (7)
H14A	0.7254	0.6932	−0.2571	0.065*
C15	0.79142 (18)	0.5604 (3)	−0.27977 (16)	0.0640 (8)
H15A	0.7548	0.5411	−0.3276	0.077*
C16	0.8614 (2)	0.4994 (2)	−0.25188 (16)	0.0611 (8)
H16A	0.8736	0.4382	−0.2808	0.073*
C17	0.91456 (17)	0.52619 (19)	−0.18201 (15)	0.0480 (7)
H17A	0.9626	0.4827	−0.1628	0.058*
C18	0.86601 (14)	0.61354 (16)	0.20231 (13)	0.0300 (5)
C19	0.92140 (14)	0.64100 (18)	0.27169 (13)	0.0346 (5)
H19A	0.9202	0.6148	0.3228	0.042*
C20	0.97809 (14)	0.71310 (16)	0.25209 (13)	0.0323 (5)
C21	1.04815 (15)	0.77291 (19)	0.30342 (14)	0.0431 (6)
H21A	1.0385	0.8510	0.2969	0.065*
H21B	1.1015	0.7539	0.2888	0.065*
H21C	1.0504	0.7530	0.3583	0.065*
C22	0.79528 (14)	0.53684 (16)	0.18952 (13)	0.0318 (5)
C23	0.75279 (17)	0.5145 (2)	0.24959 (16)	0.0481 (6)
H23A	0.7696	0.5486	0.2992	0.058*
C24	0.68578 (18)	0.4423 (2)	0.23680 (17)	0.0600 (8)
H24A	0.6570	0.4270	0.2780	0.072*
C25	0.66086 (18)	0.3931 (2)	0.16536 (17)	0.0547 (7)
H25A	0.6144	0.3447	0.1568	0.066*
C26	0.70296 (16)	0.41381 (18)	0.10604 (16)	0.0442 (6)
H26A	0.6858	0.3792	0.0566	0.053*
C27	0.77029 (14)	0.48485 (17)	0.11794 (14)	0.0351 (6)
H27A	0.7996	0.4981	0.0768	0.042*
C28	0.83466 (15)	0.99171 (17)	0.05226 (12)	0.0330 (5)
C29	0.90126 (15)	1.06349 (18)	0.07509 (13)	0.0379 (6)
H29A	0.8981	1.1403	0.0744	0.046*
C30	0.97251 (15)	1.00187 (17)	0.09878 (13)	0.0348 (6)
C31	1.06169 (15)	1.03660 (19)	0.12619 (15)	0.0446 (6)
H31A	1.0975	0.9725	0.1386	0.067*
H31B	1.0662	1.0817	0.1732	0.067*
H31C	1.0799	1.0784	0.0847	0.067*
C32	0.74580 (14)	1.02015 (17)	0.02264 (13)	0.0335 (5)
C33	0.71553 (16)	1.11925 (18)	0.04451 (14)	0.0410 (6)
H33A	0.7523	1.1667	0.0782	0.049*
C34	0.63253 (16)	1.14877 (19)	0.01753 (15)	0.0465 (7)
H34A	0.6131	1.2168	0.0322	0.056*
C35	0.57777 (16)	1.08049 (18)	−0.03043 (15)	0.0451 (7)
H35A	0.5206	1.1004	−0.0484	0.054*
C36	0.60729 (16)	0.98283 (19)	−0.05190 (15)	0.0476 (7)
H36A	0.5701	0.9351	−0.0850	0.057*
C37	0.69034 (15)	0.95342 (19)	−0.02595 (14)	0.0422 (6)
H37A	0.7095	0.8860	−0.0419	0.051*
B	1.00221 (17)	0.79415 (19)	0.11767 (16)	0.0327 (6)
H1BO	1.0673 (11)	0.8177 (13)	0.1481 (10)	0.044 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn	0.02610 (15)	0.03474 (14)	0.02890 (15)	−0.00106 (11)	0.00439 (11)	0.00005 (11)
S	0.0285 (3)	0.0434 (3)	0.0332 (3)	−0.0023 (3)	0.0032 (3)	−0.0030 (3)
N1	0.0259 (11)	0.0359 (10)	0.0330 (11)	−0.0001 (8)	0.0072 (9)	−0.0008 (8)
N2	0.0249 (11)	0.0376 (10)	0.0343 (11)	−0.0019 (9)	0.0043 (9)	0.0007 (9)
N3	0.0252 (11)	0.0363 (10)	0.0297 (11)	−0.0036 (8)	0.0038 (9)	−0.0004 (8)
N4	0.0238 (10)	0.0344 (9)	0.0295 (10)	−0.0002 (8)	0.0020 (8)	−0.0010 (8)
N5	0.0276 (11)	0.0346 (10)	0.0320 (11)	0.0010 (8)	0.0052 (9)	0.0027 (8)
N6	0.0263 (11)	0.0344 (10)	0.0323 (11)	−0.0034 (8)	0.0048 (9)	−0.0003 (8)
C1	0.0306 (14)	0.0379 (12)	0.0428 (15)	0.0074 (11)	0.0096 (11)	0.0087 (11)
C2	0.0381 (16)	0.0530 (15)	0.0410 (15)	0.0025 (12)	0.0084 (12)	0.0014 (12)
C3	0.060 (2)	0.0594 (16)	0.0454 (16)	0.0136 (15)	0.0175 (15)	0.0050 (13)
C4	0.061 (2)	0.0556 (18)	0.066 (2)	0.0213 (15)	0.0344 (17)	0.0220 (15)
C5	0.0377 (17)	0.0513 (16)	0.091 (2)	0.0055 (13)	0.0265 (17)	0.0224 (16)
C6	0.0357 (16)	0.0387 (13)	0.0659 (19)	−0.0008 (12)	0.0107 (14)	0.0036 (12)
C7	0.092 (3)	0.109 (3)	0.102 (3)	0.025 (2)	0.070 (2)	0.030 (2)
C8	0.0358 (15)	0.0338 (12)	0.0345 (14)	0.0019 (10)	0.0103 (11)	0.0050 (10)
C9	0.0363 (15)	0.0444 (14)	0.0417 (15)	0.0078 (11)	0.0124 (12)	−0.0018 (11)
C10	0.0304 (14)	0.0390 (12)	0.0409 (15)	0.0030 (11)	0.0097 (12)	0.0060 (11)
C11	0.0315 (15)	0.0624 (16)	0.0493 (17)	0.0065 (12)	0.0094 (13)	−0.0028 (13)
C12	0.0364 (15)	0.0364 (12)	0.0338 (14)	−0.0027 (10)	0.0124 (11)	−0.0007 (10)
C13	0.0375 (16)	0.0542 (14)	0.0350 (14)	0.0051 (12)	0.0118 (12)	−0.0039 (11)
C14	0.0362 (17)	0.091 (2)	0.0363 (16)	0.0083 (14)	0.0070 (13)	−0.0078 (14)
C15	0.050 (2)	0.096 (2)	0.0432 (17)	−0.0062 (17)	0.0027 (15)	−0.0202 (16)
C16	0.072 (2)	0.0587 (17)	0.0509 (19)	0.0013 (15)	0.0087 (16)	−0.0222 (14)
C17	0.0527 (18)	0.0462 (15)	0.0446 (16)	0.0072 (13)	0.0086 (14)	−0.0065 (12)
C18	0.0293 (13)	0.0301 (11)	0.0311 (13)	0.0045 (9)	0.0069 (11)	0.0014 (9)
C19	0.0322 (14)	0.0423 (13)	0.0293 (13)	0.0028 (10)	0.0061 (11)	0.0029 (10)
C20	0.0293 (13)	0.0358 (13)	0.0306 (13)	0.0046 (10)	0.0029 (10)	−0.0015 (10)
C21	0.0378 (15)	0.0543 (14)	0.0349 (13)	−0.0027 (12)	0.0016 (11)	−0.0046 (12)
C22	0.0300 (14)	0.0297 (11)	0.0361 (14)	0.0050 (9)	0.0072 (11)	0.0059 (10)
C23	0.0513 (17)	0.0565 (15)	0.0390 (15)	−0.0075 (13)	0.0148 (13)	0.0028 (12)
C24	0.056 (2)	0.0752 (19)	0.0548 (19)	−0.0224 (16)	0.0263 (16)	0.0071 (16)
C25	0.0493 (18)	0.0542 (16)	0.063 (2)	−0.0186 (13)	0.0170 (16)	0.0051 (14)
C26	0.0434 (16)	0.0395 (13)	0.0492 (16)	−0.0076 (11)	0.0086 (13)	−0.0031 (12)
C27	0.0337 (14)	0.0338 (12)	0.0392 (14)	0.0007 (10)	0.0108 (11)	0.0024 (10)
C28	0.0391 (15)	0.0337 (12)	0.0277 (13)	0.0012 (11)	0.0105 (11)	0.0026 (9)
C29	0.0434 (16)	0.0303 (12)	0.0403 (14)	−0.0030 (11)	0.0090 (12)	0.0022 (10)
C30	0.0392 (15)	0.0363 (13)	0.0299 (13)	−0.0080 (11)	0.0094 (11)	0.0014 (10)
C31	0.0413 (16)	0.0392 (13)	0.0525 (17)	−0.0104 (11)	0.0078 (13)	−0.0012 (12)
C32	0.0368 (15)	0.0354 (12)	0.0289 (13)	−0.0001 (10)	0.0080 (11)	0.0075 (10)
C33	0.0419 (16)	0.0341 (13)	0.0462 (16)	0.0004 (11)	0.0069 (13)	−0.0016 (11)
C34	0.0484 (18)	0.0363 (13)	0.0550 (17)	0.0051 (12)	0.0110 (14)	−0.0009 (12)
C35	0.0389 (16)	0.0427 (14)	0.0521 (17)	0.0064 (12)	0.0055 (13)	0.0129 (12)
C36	0.0420 (17)	0.0438 (14)	0.0514 (17)	0.0013 (12)	−0.0036 (13)	−0.0043 (12)
C37	0.0417 (17)	0.0380 (14)	0.0435 (15)	0.0060 (11)	0.0006 (13)	−0.0036 (11)
B	0.0286 (16)	0.0336 (15)	0.0353 (16)	−0.0014 (11)	0.0049 (12)	0.0018 (11)

Geometric parameters (Å, º) top

Zn—N1	2.0380 (19)	C15—C16	1.368 (4)
Zn—N3	2.0575 (17)	C15—H15A	0.9500
Zn—N5	2.0880 (17)	C16—C17	1.381 (3)
Zn—S	2.2289 (6)	C16—H16A	0.9500
S—C1	1.773 (2)	C17—H17A	0.9500
N1—C8	1.345 (3)	C18—C19	1.394 (3)
N1—N2	1.375 (2)	C18—C22	1.471 (3)
N2—C10	1.355 (3)	C19—C20	1.372 (3)
N2—B	1.544 (3)	C19—H19A	0.9500
N3—C18	1.350 (3)	C20—C21	1.492 (3)
N3—N4	1.376 (2)	C21—H21A	0.9800
N4—C20	1.357 (3)	C21—H21B	0.9800
N4—B	1.553 (3)	C21—H21C	0.9800
N5—C28	1.357 (3)	C22—C27	1.387 (3)
N5—N6	1.385 (2)	C22—C23	1.392 (3)
N6—C30	1.357 (3)	C23—C24	1.389 (3)
N6—B	1.540 (3)	C23—H23A	0.9500
C1—C6	1.389 (3)	C24—C25	1.369 (4)
C1—C2	1.394 (3)	C24—H24A	0.9500
C2—C3	1.381 (3)	C25—C26	1.372 (3)
C2—H2A	0.9500	C25—H25A	0.9500
C3—C4	1.392 (4)	C26—C27	1.384 (3)
C3—H3A	0.9500	C26—H26A	0.9500
C4—C5	1.381 (4)	C27—H27A	0.9500
C4—C7	1.509 (4)	C28—C29	1.393 (3)
C5—C6	1.390 (4)	C28—C32	1.474 (3)
C5—H5A	0.9500	C29—C30	1.377 (3)
C6—H6A	0.9500	C29—H29A	0.9500
C7—H7A	0.9800	C30—C31	1.493 (3)
C7—H7B	0.9800	C31—H31A	0.9800
C7—H7C	0.9800	C31—H31B	0.9800
C8—C9	1.390 (3)	C31—H31C	0.9800
C8—C12	1.472 (3)	C32—C37	1.377 (3)
C9—C10	1.374 (3)	C32—C33	1.400 (3)
C9—H9A	0.9500	C33—C34	1.384 (3)
C10—C11	1.497 (3)	C33—H33A	0.9500
C11—H11A	0.9800	C34—C35	1.377 (3)
C11—H11B	0.9800	C34—H34A	0.9500
C11—H11C	0.9800	C35—C36	1.377 (3)
C12—C13	1.383 (3)	C35—H35A	0.9500
C12—C17	1.398 (3)	C36—C37	1.382 (3)
C13—C14	1.381 (3)	C36—H36A	0.9500
C13—H13A	0.9500	C37—H37A	0.9500
C14—C15	1.391 (4)	B—H1BO	1.120 (17)
C14—H14A	0.9500

N1—Zn—N3	91.59 (7)	C15—C16—H16A	119.8
N1—Zn—N5	91.08 (7)	C17—C16—H16A	119.8
N3—Zn—N5	94.66 (7)	C16—C17—C12	120.5 (2)
N1—Zn—S	120.98 (5)	C16—C17—H17A	119.8
N3—Zn—S	121.81 (5)	C12—C17—H17A	119.8
N5—Zn—S	127.46 (5)	N3—C18—C19	109.28 (19)
C1—S—Zn	102.89 (8)	N3—C18—C22	121.24 (19)
C8—N1—N2	106.47 (18)	C19—C18—C22	129.5 (2)
C8—N1—Zn	137.99 (16)	C20—C19—C18	106.9 (2)
N2—N1—Zn	112.18 (13)	C20—C19—H19A	126.6
C10—N2—N1	109.83 (18)	C18—C19—H19A	126.6
C10—N2—B	130.98 (19)	N4—C20—C19	107.37 (19)
N1—N2—B	119.15 (18)	N4—C20—C21	122.7 (2)
C18—N3—N4	106.42 (16)	C19—C20—C21	129.9 (2)
C18—N3—Zn	138.04 (15)	C20—C21—H21A	109.5
N4—N3—Zn	110.82 (12)	C20—C21—H21B	109.5
C20—N4—N3	110.01 (17)	H21A—C21—H21B	109.5
C20—N4—B	130.59 (18)	C20—C21—H21C	109.5
N3—N4—B	119.37 (17)	H21A—C21—H21C	109.5
C28—N5—N6	106.28 (17)	H21B—C21—H21C	109.5
C28—N5—Zn	142.37 (15)	C27—C22—C23	118.9 (2)
N6—N5—Zn	110.39 (12)	C27—C22—C18	120.8 (2)
C30—N6—N5	109.81 (17)	C23—C22—C18	120.3 (2)
C30—N6—B	129.15 (19)	C24—C23—C22	119.9 (3)
N5—N6—B	120.81 (17)	C24—C23—H23A	120.1
C6—C1—C2	117.6 (2)	C22—C23—H23A	120.1
C6—C1—S	118.4 (2)	C25—C24—C23	120.5 (3)
C2—C1—S	123.99 (19)	C25—C24—H24A	119.7
C3—C2—C1	121.2 (3)	C23—C24—H24A	119.7
C3—C2—H2A	119.4	C24—C25—C26	120.0 (2)
C1—C2—H2A	119.4	C24—C25—H25A	120.0
C2—C3—C4	121.5 (3)	C26—C25—H25A	120.0
C2—C3—H3A	119.3	C25—C26—C27	120.3 (2)
C4—C3—H3A	119.3	C25—C26—H26A	119.9
C5—C4—C3	117.0 (3)	C27—C26—H26A	119.9
C5—C4—C7	121.9 (3)	C26—C27—C22	120.4 (2)
C3—C4—C7	121.1 (3)	C26—C27—H27A	119.8
C4—C5—C6	122.1 (3)	C22—C27—H27A	119.8
C4—C5—H5A	118.9	N5—C28—C29	109.3 (2)
C6—C5—H5A	118.9	N5—C28—C32	123.96 (19)
C5—C6—C1	120.6 (3)	C29—C28—C32	126.7 (2)
C5—C6—H6A	119.7	C30—C29—C28	106.94 (19)
C1—C6—H6A	119.7	C30—C29—H29A	126.5
C4—C7—H7A	109.5	C28—C29—H29A	126.5
C4—C7—H7B	109.5	N6—C30—C29	107.6 (2)
H7A—C7—H7B	109.5	N6—C30—C31	122.6 (2)
C4—C7—H7C	109.5	C29—C30—C31	129.8 (2)
H7A—C7—H7C	109.5	C30—C31—H31A	109.5
H7B—C7—H7C	109.5	C30—C31—H31B	109.5
N1—C8—C9	109.5 (2)	H31A—C31—H31B	109.5
N1—C8—C12	121.9 (2)	C30—C31—H31C	109.5
C9—C8—C12	128.5 (2)	H31A—C31—H31C	109.5
C10—C9—C8	106.7 (2)	H31B—C31—H31C	109.5
C10—C9—H9A	126.7	C37—C32—C33	117.9 (2)
C8—C9—H9A	126.7	C37—C32—C28	123.0 (2)
N2—C10—C9	107.5 (2)	C33—C32—C28	119.1 (2)
N2—C10—C11	123.1 (2)	C34—C33—C32	120.6 (2)
C9—C10—C11	129.4 (2)	C34—C33—H33A	119.7
C10—C11—H11A	109.5	C32—C33—H33A	119.7
C10—C11—H11B	109.5	C35—C34—C33	120.7 (2)
H11A—C11—H11B	109.5	C35—C34—H34A	119.7
C10—C11—H11C	109.5	C33—C34—H34A	119.7
H11A—C11—H11C	109.5	C36—C35—C34	118.8 (2)
H11B—C11—H11C	109.5	C36—C35—H35A	120.6
C13—C12—C17	118.4 (2)	C34—C35—H35A	120.6
C13—C12—C8	122.0 (2)	C35—C36—C37	120.8 (2)
C17—C12—C8	119.5 (2)	C35—C36—H36A	119.6
C14—C13—C12	121.1 (2)	C37—C36—H36A	119.6
C14—C13—H13A	119.4	C32—C37—C36	121.2 (2)
C12—C13—H13A	119.4	C32—C37—H37A	119.4
C13—C14—C15	119.6 (3)	C36—C37—H37A	119.4
C13—C14—H14A	120.2	N6—B—N2	109.41 (18)
C15—C14—H14A	120.2	N6—B—N4	108.39 (19)
C16—C15—C14	119.9 (3)	N2—B—N4	109.04 (17)
C16—C15—H15A	120.1	N6—B—H1BO	110.1 (9)
C14—C15—H15A	120.1	N2—B—H1BO	109.1 (9)
C15—C16—C17	120.5 (3)	N4—B—H1BO	110.8 (9)

Experimental details

Crystal data
Chemical formula	[Zn(C₃₀H₂₈BN₆)(C₇H₇S)]
M_r	671.95
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	183
a, b, c (Å)	16.2448 (7), 12.3442 (3), 17.3988 (7)
β (°)	101.675 (1)
V (Å³)	3416.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.82
Crystal size (mm)	0.18 × 0.12 × 0.10

Data collection
Diffractometer	Nonius KappaCCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13913, 7635, 4579
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.087, 0.87
No. of reflections	7635
No. of parameters	422
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.41

Computer programs: COLLECT (Nonius, 1998), DENZO (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL/PC (Siemens, 1990).

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