[(S,S)-N-(1-{6-[1-(Di­methyl­amino)­ethyl]­pyridin-2-yl}ethyl)-N,N-di­methyl­amine-κ3N]­di­bromo­zinc(II)

Panosyan, F.B.; Lough, A.J.; Chin, J.

doi:10.1107/S1600536803018920

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[(S,S)-N-(1-{6-[1-(Dimethylamino)ethyl]pyridin-2-yl}ethyl)-N,N-dimethylamine-κ³N]dibromozinc(II)

F. B. Panosyan, A. J. Lough and J. Chin

The title compound, [ZnBr₂(C₁₃H₂₃N₃)], (3), was readily prepared from the reaction between ZnBr₂ and (S,S)-(1–6-[1-(dimethylamino)ethyl]-2-pyridinylethyl)-N,N-dimethylamine. (3) exists as a distorted square pyramid and crystallizes with two independent molecules in the asymmetric unit. The apical position of the square pyramid is occupied by one of the Br atoms, with the base of the pyramid consisting of the three N atoms of the ligand and the other Br atom. This is the first reported structure determination of a compound containing the C₂-symmetric molecule (S,S)-N-(1-{6-[1-(dimethylamino)ethyl]pyridin-2-yl}ethyl)-N,N-dimethylamine.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803018920/bt6335sup1.cif Contains datablocks global, 3
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803018920/bt63353sup2.hkl Contains datablock 3

CCDC reference: 222837

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.009 Å
R factor = 0.051
wR factor = 0.131
Data-to-parameter ratio = 21.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.99
PLAT213_ALERT_2_C Atom C13A    has ADP max/min Ratio .............       3.30 prolat
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.86 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.24 Ratio
PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor ....       2.09
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         22

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.54
           From the CIF: _reflns_number_total               7418
           Count of symmetry unique reflns         4164
           Completeness (_total/calc)            178.15%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      3254
           Fraction of Friedel pairs measured     0.781
           Are heavy atom types Z>Si present          yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 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
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Zinc complexes are important in organic chemistry due to the their central role in many enantioselective reactions (Denmark & Beutner, 2002; Lebel et al., 2003; Soai, 1999) and biological systems (Auld, 2001; Lipscomb & Strater, 1996; Vallee & Auld, 1993). In our ongoing program that aims at developing ligands for molecular recognition of biologically important compounds (Chin et al., 1999; Mancin & Chin, 2002), we wish to report the synthesis and the X-ray analysis of complex (3) from the optically active C2-symmetric ligand (S,S)—N-(1-{6-[1-(dimethylamino)ethyl]pyridin-2-yl}ethyl)-N,N-dimethylamine, (2), and zinc(II) bromide.

Ligand (2) was prepared from the readily available chiral diol (R,R)-(BHEP), (1) (Brown et al., 1997), where BHEP = 2,6-bis(1-hydroxyethyl)pyridine, through its reaction with methanesulfonic anhydride and dimethylamine in acetonitrile (see Scheme). The substitution reaction proceeded through conversion of stereochemistry to afford the (S,S) enantiomer of ligand (2), which was then complexed with zinc(II) bromide to produce compound (3).

In the crystal structure of (3), there are two molecules in the asymmetric unit, A and B (Figs. 1 and 2). The coordination geometry of compound (3) is a distorted square pyramid, with the apical position occupied by a Br atom (Br1). The three N atoms of the ligand and the other Br atom (Br2) occupy the base of the pyramid. The Zn atom is displaced by 0.668 (2) and 0.675 (2) Å in molecules A and B, respectively, towards atom Br1 from the least-squares plane formed by N1/N2/N3/Br2. The maximum deviations from these planes are for atoms N2A [0.027 (3) Å] and N2B [0.103 Å]. An analysis (Cremer & Pople, 1975) of the puckering of the five-membered metallacycle (Zn1/N1/C1/C2/N2), where the C atom (C10) is equatorial to the chelate ring, gives Q_t values of 0.412 (5) and 0.424 (5) Å for molecules A and B, respectively. The puckering of the five-membered metallacycle (Zn1/N3/C7/C6/N2), where the C atom (C11) is axial to the chelate ring, gives Q_t values of 0.404 (6) and 0.414 (5) Å for molecules A and B, respectively. The conformations of each five-membered ring in both molecules is `envelope' with a local pseudo-twofold axis running along N1 and the mid-point of the C2—N2 bond or N3 and the mid-point of the C6—N2 bond (Duax et al., 1976). The angles N2—Zn1—N1 of 76.00 (17) and 75.61 (19)°, and N2—Zn1—N3 of 74.85 (18) and 74.15 (19)° for molecules A and B, respectively, are considerably smaller than the ideal angle of 90° for a square pyramid. These angles are due to the formation of strained five-membered chelate rings and the distortion in the square pyramid environment around the Zn atom. The Zn—N_pyridine bond length in molecules A and B [average 2.106 (5) Å], is comparable to the corresponding bond lengths in other ligands with pyridine complexed to Zn^II (Canary et al., 1998; Comba et al., 2002). The only differences between the two molecules in (3) are the values of some of the angles at the Zn center; the most notable of these being N3A—Zn1A—Br1A of 108.90 (16)° and N3B—Zn1B—Br1B of 113.89 (14)°. These differences which may be apparent on viewing Figs. 1 and 2 can only be attributable to packing forces.

Experimental top

2,6-Bis(1-hydroxyethyl)pyridine, (1) (1.21 g, 7.21 mmol), was dissolved in 40 ml dry acetonitrile. Pyridine (3.00 ml, 37.2 mmol) was added to this solution and the mixture was cooled to 273 K in an ice bath. Methanesulfonic anhydride (3.00 g,16.7 mmol) was added to this mixture under an atmosphere of argon. The clear yellow solution turned cloudy after 5 min. This mixture was allowed to stir at room temperature for an additional 30 min and the precipitate was filtered off. Dimethylamine (20 ml, 40.0 mmol) from a 2 M tetrahydrofuran solution was added to the golden brown filtrate and this mixture was allowed to stir at room temperature for 24 h. The precipitate was filtered off and the organic solvents removed under reduced pressure. The remaining residue was partitioned between (30 ml) chloroform and (20 ml) saturated aqueous solution of Na₂CO₃. The aqueous layer was further extracted with (30 ml) chloroform and the two organic extracts were combined, dried over anhydrous sodium sulfate and the solvent evaporated to afford the crude product, (2), as a brown oil. This oil was chromatographed on silica with dichloromethane/methanol (8:2) as eluant to afford the pure product (2) as a yellow oil (1.31 g, 82%). ¹H NMR, 300 MHz (CDCl₃): 7.60 (t, J = 7.7 Hz, 1H), 7.21 (d, J = 7.7 Hz, 2H), 3.48 (q, J = 6.6 Hz, 2H), 2.24 (s, 12H), 1.36 (d, J = 6.6 Hz, 6H). ¹³C NMR, 100 MHz (CDCl₃): δ 162.5, 136.6, 119.8, 67.2, 43.1, 19.1. Zinc(II) bromide (183 mg, 0.813 mmol) in 1.5 ml H₂O was added to (2) (18.0 mg, 81.3 µmol). The precipitate was collected and dissolved in hot ethanol (2.0 ml). Slow evaporation of the ethanol at room temperature afforded crystals of (3) suitable for X-ray analysis.

Computing details top

Data collection: COLLECT (Nonius, 1997-2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXT.

Figures top

	Fig. 1. View of molecule A of (3), with the crystallographic labeling scheme. Displacement ellipsoids are at the 30% probability level.
	Fig. 2. View of molecule B of (3), with the crystallographic labeling scheme. Displacement ellipsoids are at the 30% probability level.
	Fig. 3. Packing diagram (Spek, 2002) of (3), viewed bown the b axis. Colour codes: green Br, yellow Zn, blue N, and black C.

[(S,S)—N-(1-{6-[1-(Dimethylamino)ethyl]pyridin-2-yl}ethyl)-N,N- dimethylamine-κ³N]dibromozinc(II) top

Crystal data top

[ZnBr₂(C₁₃H₂₃N₃)]	F(000) = 888
M_r = 446.53	D_x = 1.718 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 24950 reflections
a = 9.9680 (2) Å	θ = 2.6–27.5°
b = 11.5077 (2) Å	µ = 6.04 mm⁻¹
c = 15.4906 (4) Å	T = 150 K
β = 103.712 (1)°	Block, colourless
V = 1726.26 (6) Å³	0.35 × 0.30 × 0.24 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	7418 independent reflections
Radiation source: fine-focus sealed tube	6981 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.064
Detector resolution: 9 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
ϕ scans and ω scans from κ offsets	h = −12→12
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −14→14
T_min = 0.131, T_max = 0.234	l = −19→20
12530 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.051	w = 1/[σ²(F_o²) + (0.0848P)² + 0.0739P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.131	(Δ/σ)_max < 0.001
S = 1.06	Δρ_max = 0.91 e Å⁻³
7418 reflections	Δρ_min = −1.64 e Å⁻³
344 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0082 (10)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983); 3292 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.021 (13)

Crystal data top

[ZnBr₂(C₁₃H₂₃N₃)]	V = 1726.26 (6) Å³
M_r = 446.53	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 9.9680 (2) Å	µ = 6.04 mm⁻¹
b = 11.5077 (2) Å	T = 150 K
c = 15.4906 (4) Å	0.35 × 0.30 × 0.24 mm
β = 103.712 (1)°

Data collection top

Nonius KappaCCD diffractometer	7418 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	6981 reflections with I > 2σ(I)
T_min = 0.131, T_max = 0.234	R_int = 0.064
12530 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.131	Δρ_max = 0.91 e Å⁻³
S = 1.06	Δρ_min = −1.64 e Å⁻³
7418 reflections	Absolute structure: Flack (1983); 3292 Friedel pairs
344 parameters	Absolute structure parameter: −0.021 (13)
1 restraint

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
Zn1A	0.10746 (5)	0.63162 (6)	0.34857 (4)	0.02934 (15)
Br1A	0.01456 (6)	0.72224 (6)	0.20732 (4)	0.04120 (16)
Br2A	−0.07060 (6)	0.63257 (6)	0.43285 (4)	0.04478 (17)
N1A	0.2394 (4)	0.7659 (4)	0.4323 (3)	0.0296 (9)
N2A	0.3106 (4)	0.5837 (4)	0.3455 (3)	0.0279 (8)
N3A	0.1006 (5)	0.4383 (5)	0.3306 (4)	0.0408 (11)
C1A	0.3676 (5)	0.7783 (5)	0.3984 (3)	0.0306 (10)
H1AA	0.3403	0.8221	0.3412	0.037*
C2A	0.4129 (5)	0.6591 (5)	0.3756 (3)	0.0279 (10)
C3A	0.5480 (5)	0.6280 (5)	0.3796 (3)	0.0326 (10)
H3AA	0.6215	0.6806	0.4021	0.039*
C4A	0.5746 (6)	0.5185 (6)	0.3500 (4)	0.0350 (12)
H4AA	0.6672	0.4955	0.3531	0.042*
C5A	0.4683 (6)	0.4430 (6)	0.3163 (4)	0.0364 (12)
H5AA	0.4853	0.3693	0.2933	0.044*
C6A	0.3346 (5)	0.4782 (5)	0.3169 (3)	0.0288 (10)
C7A	0.2091 (6)	0.4037 (6)	0.2825 (4)	0.0412 (14)
H7AA	0.2339	0.3202	0.2950	0.049*
C8A	0.1649 (7)	0.8779 (6)	0.4263 (5)	0.0436 (14)
H8AA	0.2239	0.9358	0.4634	0.065*
H8AB	0.0802	0.8676	0.4471	0.065*
H8AC	0.1413	0.9044	0.3645	0.065*
C9A	0.2725 (6)	0.7248 (7)	0.5252 (4)	0.0433 (14)
H9AA	0.3304	0.7824	0.5633	0.065*
H9AB	0.3222	0.6508	0.5293	0.065*
H9AC	0.1868	0.7138	0.5448	0.065*
C10A	0.4842 (6)	0.8475 (6)	0.4581 (4)	0.0428 (14)
H10A	0.4494	0.9237	0.4708	0.064*
H10B	0.5594	0.8579	0.4280	0.064*
H10C	0.5186	0.8053	0.5139	0.064*
C11A	0.1618 (8)	0.4226 (8)	0.1811 (5)	0.059 (2)
H11A	0.2356	0.3988	0.1529	0.088*
H11B	0.1407	0.5050	0.1688	0.088*
H11C	0.0790	0.3760	0.1572	0.088*
C12A	0.1414 (8)	0.3859 (8)	0.4199 (6)	0.063 (2)
H12A	0.1394	0.3011	0.4146	0.095*
H12B	0.0770	0.4107	0.4552	0.095*
H12C	0.2350	0.4113	0.4492	0.095*
C13A	−0.0395 (7)	0.3935 (8)	0.2854 (8)	0.080 (3)
H13A	−0.0357	0.3088	0.2795	0.120*
H13B	−0.0689	0.4287	0.2263	0.120*
H13C	−0.1056	0.4136	0.3208	0.120*
Zn1B	0.46597 (6)	0.08880 (6)	0.16004 (4)	0.03171 (16)
Br1B	0.40421 (6)	0.10618 (5)	0.30084 (4)	0.03968 (16)
Br2B	0.48588 (7)	0.28215 (6)	0.09799 (4)	0.04563 (17)
N1B	0.2658 (5)	0.0407 (5)	0.0663 (3)	0.0349 (10)
N2B	0.4752 (5)	−0.0928 (4)	0.1491 (3)	0.0322 (9)
N3B	0.6917 (5)	0.0456 (5)	0.1721 (3)	0.0370 (10)
C1B	0.2287 (5)	−0.0774 (6)	0.0917 (4)	0.0336 (11)
H1BA	0.1892	−0.0676	0.1449	0.040*
C2B	0.3572 (6)	−0.1511 (5)	0.1211 (3)	0.0315 (11)
C3B	0.3569 (6)	−0.2715 (6)	0.1221 (3)	0.0357 (11)
H3BA	0.2730	−0.3132	0.1024	0.043*
C4B	0.4806 (7)	−0.3302 (6)	0.1524 (4)	0.0391 (12)
H4BA	0.4822	−0.4127	0.1532	0.047*
C5B	0.6025 (6)	−0.2677 (5)	0.1815 (4)	0.0369 (11)
H5BA	0.6883	−0.3063	0.2024	0.044*
C6B	0.5951 (6)	−0.1472 (5)	0.1792 (4)	0.0323 (11)
C7B	0.7193 (6)	−0.0704 (5)	0.2124 (4)	0.0377 (12)
H7BA	0.8005	−0.1051	0.1943	0.045*
C8B	0.1588 (7)	0.1260 (7)	0.0706 (5)	0.0489 (15)
H8BA	0.0721	0.1036	0.0293	0.073*
H8BB	0.1873	0.2028	0.0542	0.073*
H8BC	0.1452	0.1288	0.1312	0.073*
C9B	0.2938 (7)	0.0430 (7)	−0.0233 (4)	0.0465 (14)
H9BA	0.2095	0.0225	−0.0677	0.070*
H9BB	0.3667	−0.0132	−0.0259	0.070*
H9BC	0.3237	0.1211	−0.0357	0.070*
C10B	0.1171 (7)	−0.1370 (7)	0.0203 (5)	0.0523 (17)
H10D	0.0364	−0.0859	0.0036	0.078*
H10E	0.0901	−0.2102	0.0438	0.078*
H10F	0.1534	−0.1529	−0.0320	0.078*
C11B	0.7505 (7)	−0.0655 (6)	0.3156 (4)	0.0451 (14)
H11D	0.8313	−0.0161	0.3381	0.068*
H11E	0.7694	−0.1441	0.3398	0.068*
H11F	0.6706	−0.0333	0.3340	0.068*
C12B	0.7049 (7)	0.0362 (7)	0.0761 (5)	0.0480 (15)
H12D	0.8006	0.0175	0.0755	0.072*
H12E	0.6791	0.1104	0.0456	0.072*
H12F	0.6436	−0.0252	0.0455	0.072*
C13B	0.7874 (7)	0.1340 (7)	0.2166 (5)	0.0507 (16)
H13D	0.8823	0.1091	0.2192	0.076*
H13E	0.7756	0.1452	0.2771	0.076*
H13F	0.7689	0.2072	0.1837	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1A	0.0165 (2)	0.0351 (3)	0.0365 (3)	0.0002 (2)	0.0066 (2)	−0.0004 (2)
Br1A	0.0310 (3)	0.0512 (4)	0.0404 (3)	0.0109 (2)	0.0063 (2)	0.0049 (2)
Br2A	0.0252 (2)	0.0551 (4)	0.0593 (4)	−0.0052 (2)	0.0205 (2)	−0.0018 (3)
N1A	0.0207 (19)	0.036 (2)	0.034 (2)	−0.0004 (16)	0.0103 (16)	−0.0060 (17)
N2A	0.0164 (17)	0.035 (2)	0.0325 (19)	0.0017 (16)	0.0055 (14)	−0.0016 (17)
N3A	0.020 (2)	0.038 (3)	0.064 (3)	−0.0025 (18)	0.010 (2)	0.002 (2)
C1A	0.023 (2)	0.036 (3)	0.034 (2)	−0.003 (2)	0.0086 (19)	−0.005 (2)
C2A	0.017 (2)	0.039 (3)	0.029 (2)	0.0009 (18)	0.0075 (16)	0.002 (2)
C3A	0.019 (2)	0.044 (3)	0.036 (2)	0.000 (2)	0.0080 (17)	0.007 (2)
C4A	0.021 (2)	0.048 (3)	0.038 (3)	0.004 (2)	0.0108 (19)	0.007 (2)
C5A	0.026 (2)	0.047 (3)	0.037 (3)	0.011 (2)	0.010 (2)	0.003 (2)
C6A	0.020 (2)	0.031 (3)	0.035 (2)	0.0055 (18)	0.0064 (18)	0.001 (2)
C7A	0.026 (3)	0.035 (3)	0.058 (4)	0.005 (2)	0.001 (2)	−0.012 (3)
C8A	0.037 (3)	0.040 (3)	0.056 (4)	0.002 (3)	0.015 (3)	−0.011 (3)
C9A	0.034 (3)	0.067 (4)	0.032 (3)	−0.015 (3)	0.015 (2)	−0.006 (3)
C10A	0.029 (3)	0.050 (4)	0.050 (3)	−0.012 (2)	0.010 (2)	−0.012 (3)
C11A	0.042 (3)	0.074 (5)	0.051 (4)	0.015 (3)	−0.007 (3)	−0.022 (4)
C12A	0.042 (4)	0.059 (5)	0.095 (6)	0.011 (3)	0.028 (4)	0.036 (4)
C13A	0.022 (3)	0.058 (5)	0.150 (9)	−0.014 (3)	0.003 (4)	−0.038 (5)
Zn1B	0.0298 (3)	0.0307 (3)	0.0364 (3)	0.0015 (2)	0.0114 (2)	0.0000 (2)
Br1B	0.0444 (3)	0.0414 (3)	0.0361 (3)	0.0076 (2)	0.0152 (2)	0.0001 (2)
Br2B	0.0551 (4)	0.0352 (3)	0.0513 (3)	0.0008 (3)	0.0221 (3)	0.0061 (2)
N1B	0.031 (2)	0.039 (2)	0.035 (2)	0.0029 (19)	0.0061 (18)	0.0015 (19)
N2B	0.029 (2)	0.035 (2)	0.035 (2)	−0.0039 (18)	0.0125 (18)	−0.0042 (18)
N3B	0.028 (2)	0.038 (3)	0.046 (3)	−0.0029 (19)	0.0108 (19)	−0.004 (2)
C1B	0.024 (2)	0.046 (3)	0.030 (2)	−0.001 (2)	0.0047 (18)	0.000 (2)
C2B	0.035 (3)	0.037 (3)	0.025 (2)	−0.002 (2)	0.0109 (19)	0.0000 (19)
C3B	0.039 (3)	0.040 (3)	0.029 (2)	−0.012 (2)	0.011 (2)	−0.003 (2)
C4B	0.050 (3)	0.032 (3)	0.038 (3)	−0.007 (2)	0.017 (2)	−0.001 (2)
C5B	0.042 (3)	0.031 (3)	0.042 (3)	0.004 (2)	0.018 (2)	0.004 (2)
C6B	0.032 (3)	0.030 (3)	0.036 (3)	0.003 (2)	0.013 (2)	0.003 (2)
C7B	0.028 (2)	0.039 (3)	0.048 (3)	0.006 (2)	0.012 (2)	0.000 (2)
C8B	0.036 (3)	0.058 (4)	0.052 (3)	0.014 (3)	0.009 (2)	0.004 (3)
C9B	0.045 (3)	0.056 (4)	0.038 (3)	0.001 (3)	0.009 (3)	0.004 (3)
C10B	0.037 (3)	0.057 (4)	0.053 (4)	−0.010 (3)	−0.008 (3)	0.007 (3)
C11B	0.037 (3)	0.051 (4)	0.043 (3)	0.000 (3)	0.003 (2)	0.006 (3)
C12B	0.042 (3)	0.059 (4)	0.051 (3)	−0.005 (3)	0.026 (3)	−0.001 (3)
C13B	0.034 (3)	0.050 (4)	0.065 (4)	−0.012 (3)	0.006 (3)	−0.001 (3)

Geometric parameters (Å, º) top

Zn1A—N2A	2.110 (4)	Zn1B—N2B	2.101 (5)
Zn1A—N1A	2.234 (4)	Zn1B—N1B	2.241 (5)
Zn1A—N3A	2.241 (6)	Zn1B—N3B	2.269 (5)
Zn1A—Br1A	2.4025 (8)	Zn1B—Br1B	2.4109 (8)
Zn1A—Br2A	2.4401 (8)	Zn1B—Br2B	2.4504 (9)
N1A—C9A	1.477 (7)	N1B—C8B	1.462 (8)
N1A—C8A	1.479 (8)	N1B—C9B	1.480 (8)
N1A—C1A	1.499 (6)	N1B—C1B	1.486 (8)
N2A—C6A	1.334 (7)	N2B—C6B	1.332 (7)
N2A—C2A	1.336 (7)	N2B—C2B	1.334 (7)
N3A—C12A	1.475 (10)	N3B—C13B	1.452 (8)
N3A—C13A	1.498 (8)	N3B—C7B	1.472 (8)
N3A—C7A	1.504 (8)	N3B—C12B	1.527 (8)
C1A—C2A	1.512 (8)	C1B—C2B	1.514 (8)
C1A—C10A	1.526 (7)	C1B—C10B	1.531 (8)
C1A—H1AA	1.0000	C1B—H1BA	1.0000
C2A—C3A	1.381 (7)	C2B—C3B	1.385 (9)
C3A—C4A	1.388 (9)	C3B—C4B	1.387 (9)
C3A—H3AA	0.9500	C3B—H3BA	0.9500
C4A—C5A	1.374 (9)	C4B—C5B	1.392 (9)
C4A—H4AA	0.9500	C4B—H4BA	0.9500
C5A—C6A	1.395 (7)	C5B—C6B	1.388 (8)
C5A—H5AA	0.9500	C5B—H5BA	0.9500
C6A—C7A	1.506 (8)	C6B—C7B	1.508 (8)
C7A—C11A	1.546 (10)	C7B—C11B	1.556 (9)
C7A—H7AA	1.0000	C7B—H7BA	1.0000
C8A—H8AA	0.9800	C8B—H8BA	0.9800
C8A—H8AB	0.9800	C8B—H8BB	0.9800
C8A—H8AC	0.9800	C8B—H8BC	0.9800
C9A—H9AA	0.9800	C9B—H9BA	0.9800
C9A—H9AB	0.9800	C9B—H9BB	0.9800
C9A—H9AC	0.9800	C9B—H9BC	0.9800
C10A—H10A	0.9800	C10B—H10D	0.9800
C10A—H10B	0.9800	C10B—H10E	0.9800
C10A—H10C	0.9800	C10B—H10F	0.9800
C11A—H11A	0.9800	C11B—H11D	0.9800
C11A—H11B	0.9800	C11B—H11E	0.9800
C11A—H11C	0.9800	C11B—H11F	0.9800
C12A—H12A	0.9800	C12B—H12D	0.9800
C12A—H12B	0.9800	C12B—H12E	0.9800
C12A—H12C	0.9800	C12B—H12F	0.9800
C13A—H13A	0.9800	C13B—H13D	0.9800
C13A—H13B	0.9800	C13B—H13E	0.9800
C13A—H13C	0.9800	C13B—H13F	0.9800

N2A—Zn1A—N1A	76.00 (17)	N2B—Zn1B—N1B	75.61 (19)
N2A—Zn1A—N3A	74.85 (18)	N2B—Zn1B—N3B	74.15 (19)
N1A—Zn1A—N3A	139.05 (18)	N1B—Zn1B—N3B	135.45 (19)
N2A—Zn1A—Br1A	104.93 (12)	N2B—Zn1B—Br1B	100.44 (13)
N1A—Zn1A—Br1A	105.97 (13)	N1B—Zn1B—Br1B	103.14 (13)
N3A—Zn1A—Br1A	108.90 (16)	N3B—Zn1B—Br1B	113.89 (14)
N2A—Zn1A—Br2A	146.82 (12)	N2B—Zn1B—Br2B	149.60 (13)
N1A—Zn1A—Br2A	95.11 (11)	N1B—Zn1B—Br2B	96.46 (14)
N3A—Zn1A—Br2A	93.81 (14)	N3B—Zn1B—Br2B	93.45 (14)
Br1A—Zn1A—Br2A	108.25 (3)	Br1B—Zn1B—Br2B	109.96 (3)
C9A—N1A—C8A	109.5 (5)	C8B—N1B—C9B	109.4 (5)
C9A—N1A—C1A	111.1 (4)	C8B—N1B—C1B	111.8 (5)
C8A—N1A—C1A	110.6 (5)	C9B—N1B—C1B	112.2 (5)
C9A—N1A—Zn1A	108.0 (4)	C8B—N1B—Zn1B	110.6 (4)
C8A—N1A—Zn1A	110.4 (3)	C9B—N1B—Zn1B	105.5 (4)
C1A—N1A—Zn1A	107.2 (3)	C1B—N1B—Zn1B	107.1 (3)
C6A—N2A—C2A	121.7 (4)	C6B—N2B—C2B	121.8 (5)
C6A—N2A—Zn1A	119.6 (3)	C6B—N2B—Zn1B	119.5 (4)
C2A—N2A—Zn1A	118.7 (4)	C2B—N2B—Zn1B	118.3 (4)
C12A—N3A—C13A	108.5 (7)	C13B—N3B—C7B	113.5 (5)
C12A—N3A—C7A	106.6 (5)	C13B—N3B—C12B	108.3 (5)
C13A—N3A—C7A	112.2 (6)	C7B—N3B—C12B	107.4 (5)
C12A—N3A—Zn1A	107.2 (5)	C13B—N3B—Zn1B	114.4 (4)
C13A—N3A—Zn1A	113.4 (5)	C7B—N3B—Zn1B	108.4 (4)
C7A—N3A—Zn1A	108.7 (4)	C12B—N3B—Zn1B	104.4 (4)
N1A—C1A—C2A	108.8 (4)	N1B—C1B—C2B	110.3 (4)
N1A—C1A—C10A	115.3 (4)	N1B—C1B—C10B	113.7 (5)
C2A—C1A—C10A	112.8 (5)	C2B—C1B—C10B	112.6 (5)
N1A—C1A—H1AA	106.4	N1B—C1B—H1BA	106.6
C2A—C1A—H1AA	106.4	C2B—C1B—H1BA	106.6
C10A—C1A—H1AA	106.4	C10B—C1B—H1BA	106.6
N2A—C2A—C3A	120.2 (5)	N2B—C2B—C3B	120.2 (6)
N2A—C2A—C1A	115.2 (4)	N2B—C2B—C1B	115.8 (5)
C3A—C2A—C1A	124.6 (5)	C3B—C2B—C1B	124.0 (5)
C2A—C3A—C4A	118.8 (5)	C2B—C3B—C4B	119.1 (5)
C2A—C3A—H3AA	120.6	C2B—C3B—H3BA	120.4
C4A—C3A—H3AA	120.6	C4B—C3B—H3BA	120.4
C5A—C4A—C3A	120.6 (5)	C3B—C4B—C5B	119.7 (6)
C5A—C4A—H4AA	119.7	C3B—C4B—H4BA	120.1
C3A—C4A—H4AA	119.7	C5B—C4B—H4BA	120.1
C4A—C5A—C6A	117.7 (6)	C6B—C5B—C4B	118.1 (6)
C4A—C5A—H5AA	121.1	C6B—C5B—H5BA	120.9
C6A—C5A—H5AA	121.1	C4B—C5B—H5BA	120.9
N2A—C6A—C5A	120.9 (5)	N2B—C6B—C5B	121.1 (6)
N2A—C6A—C7A	115.8 (4)	N2B—C6B—C7B	116.1 (5)
C5A—C6A—C7A	123.2 (5)	C5B—C6B—C7B	122.8 (5)
N3A—C7A—C6A	108.0 (5)	N3B—C7B—C6B	109.4 (5)
N3A—C7A—C11A	112.6 (5)	N3B—C7B—C11B	112.0 (5)
C6A—C7A—C11A	107.9 (6)	C6B—C7B—C11B	108.7 (5)
N3A—C7A—H7AA	109.4	N3B—C7B—H7BA	108.9
C6A—C7A—H7AA	109.4	C6B—C7B—H7BA	108.9
C11A—C7A—H7AA	109.4	C11B—C7B—H7BA	108.9
N1A—C8A—H8AA	109.5	N1B—C8B—H8BA	109.5
N1A—C8A—H8AB	109.5	N1B—C8B—H8BB	109.5
H8AA—C8A—H8AB	109.5	H8BA—C8B—H8BB	109.5
N1A—C8A—H8AC	109.5	N1B—C8B—H8BC	109.5
H8AA—C8A—H8AC	109.5	H8BA—C8B—H8BC	109.5
H8AB—C8A—H8AC	109.5	H8BB—C8B—H8BC	109.5
N1A—C9A—H9AA	109.5	N1B—C9B—H9BA	109.5
N1A—C9A—H9AB	109.5	N1B—C9B—H9BB	109.5
H9AA—C9A—H9AB	109.5	H9BA—C9B—H9BB	109.5
N1A—C9A—H9AC	109.5	N1B—C9B—H9BC	109.5
H9AA—C9A—H9AC	109.5	H9BA—C9B—H9BC	109.5
H9AB—C9A—H9AC	109.5	H9BB—C9B—H9BC	109.5
C1A—C10A—H10A	109.5	C1B—C10B—H10D	109.5
C1A—C10A—H10B	109.5	C1B—C10B—H10E	109.5
H10A—C10A—H10B	109.5	H10D—C10B—H10E	109.5
C1A—C10A—H10C	109.5	C1B—C10B—H10F	109.5
H10A—C10A—H10C	109.5	H10D—C10B—H10F	109.5
H10B—C10A—H10C	109.5	H10E—C10B—H10F	109.5
C7A—C11A—H11A	109.5	C7B—C11B—H11D	109.5
C7A—C11A—H11B	109.5	C7B—C11B—H11E	109.5
H11A—C11A—H11B	109.5	H11D—C11B—H11E	109.5
C7A—C11A—H11C	109.5	C7B—C11B—H11F	109.5
H11A—C11A—H11C	109.5	H11D—C11B—H11F	109.5
H11B—C11A—H11C	109.5	H11E—C11B—H11F	109.5
N3A—C12A—H12A	109.5	N3B—C12B—H12D	109.5
N3A—C12A—H12B	109.5	N3B—C12B—H12E	109.5
H12A—C12A—H12B	109.5	H12D—C12B—H12E	109.5
N3A—C12A—H12C	109.5	N3B—C12B—H12F	109.5
H12A—C12A—H12C	109.5	H12D—C12B—H12F	109.5
H12B—C12A—H12C	109.5	H12E—C12B—H12F	109.5
N3A—C13A—H13A	109.5	N3B—C13B—H13D	109.5
N3A—C13A—H13B	109.5	N3B—C13B—H13E	109.5
H13A—C13A—H13B	109.5	H13D—C13B—H13E	109.5
N3A—C13A—H13C	109.5	N3B—C13B—H13F	109.5
H13A—C13A—H13C	109.5	H13D—C13B—H13F	109.5
H13B—C13A—H13C	109.5	H13E—C13B—H13F	109.5

Experimental details

Crystal data
Chemical formula	[ZnBr₂(C₁₃H₂₃N₃)]
M_r	446.53
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	150
a, b, c (Å)	9.9680 (2), 11.5077 (2), 15.4906 (4)
β (°)	103.712 (1)
V (Å³)	1726.26 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	6.04
Crystal size (mm)	0.35 × 0.30 × 0.24

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1995)
T_min, T_max	0.131, 0.234
No. of measured, independent and observed [I > 2σ(I)] reflections	12530, 7418, 6981
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.131, 1.06
No. of reflections	7418
No. of parameters	344
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.91, −1.64
Absolute structure	Flack (1983); 3292 Friedel pairs
Absolute structure parameter	−0.021 (13)

Computer programs: COLLECT (Nonius, 1997-2002), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXTL (Sheldrick, 2001), SHELXTL, SHELXT.

Selected geometric parameters (Å, º) top

Zn1A—N2A	2.110 (4)	Zn1B—N2B	2.101 (5)
Zn1A—N1A	2.234 (4)	Zn1B—N1B	2.241 (5)
Zn1A—N3A	2.241 (6)	Zn1B—N3B	2.269 (5)
Zn1A—Br1A	2.4025 (8)	Zn1B—Br1B	2.4109 (8)
Zn1A—Br2A	2.4401 (8)	Zn1B—Br2B	2.4504 (9)

N2A—Zn1A—N1A	76.00 (17)	N2B—Zn1B—N1B	75.61 (19)
N2A—Zn1A—N3A	74.85 (18)	N2B—Zn1B—N3B	74.15 (19)
N1A—Zn1A—N3A	139.05 (18)	N1B—Zn1B—N3B	135.45 (19)
N2A—Zn1A—Br1A	104.93 (12)	N2B—Zn1B—Br1B	100.44 (13)
N1A—Zn1A—Br1A	105.97 (13)	N1B—Zn1B—Br1B	103.14 (13)
N3A—Zn1A—Br1A	108.90 (16)	N3B—Zn1B—Br1B	113.89 (14)
N2A—Zn1A—Br2A	146.82 (12)	N2B—Zn1B—Br2B	149.60 (13)
N1A—Zn1A—Br2A	95.11 (11)	N1B—Zn1B—Br2B	96.46 (14)
N3A—Zn1A—Br2A	93.81 (14)	N3B—Zn1B—Br2B	93.45 (14)
Br1A—Zn1A—Br2A	108.25 (3)	Br1B—Zn1B—Br2B	109.96 (3)

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