Literature DB >> 23476510

Bis(azido-κN)bis-[4-(dimethyl-amino)-pyridine-κN]zinc.

Fatiha Guenifa1, Nasreddine Hadjadj, Ouahida Zeghouan, Lamia Bendjeddou, Hocine Merazig.   

Abstract

In the title complex, [Zn(N3)2(C7H10N2)2], the Zn(II) atom is coordinated by two N atoms from two 4-(dimethyl-amino)-pyridine (DMAP) ligands and by two N atoms from two azide anions in a distorted tetra-hedral coordination geometry. In the crystal, weak C-H⋯N hydrogen bonds between the DMAP and azide ligands link these discrete complex mol-ecules into a three-dimensional supra-molecular network.

Entities:  

Year:  2013        PMID： 23476510      PMCID： PMC3588442          DOI： 10.1107/S1600536813004686

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the property of complexes with a dimethyl­amino­pyridine ligand, see: Araki et al. (2005 ▶). For weak hydrogen-bonding modes, see: Bernstein et al. (1995 ▶). For related compounds, see: Fu (2000 ▶); Tyrra et al. (2003 ▶).

Experimental

Crystal data

[Zn(N3)2(C7H10N2)2] M = 393.79 Monoclinic, a = 14.819 (5) Å b = 9.610 (5) Å c = 14.555 (5) Å β = 118.158 (5)° V = 1827.5 (13) Å3 Z = 4 Mo Kα radiation μ = 1.36 mm−1 T = 293 K 0.3 × 0.2 × 0.2 mm

Data collection

Nonius KappaCCD diffractometer 15768 measured reflections 4302 independent reflections 3323 reflections with I > 2σ(I) R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.033 wR(F 2) = 0.098 S = 1.03 4302 reflections 230 parameters H-atom parameters constrained Δρmax = 0.31 e Å−3 Δρmin = −0.45 e Å−3 Data collection: KappaCCD Reference Manual (Nonius, 1998 ▶); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK ▶; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶), Mercury (Macrae et al., 2006 ▶) and POVRay (Persistence of Vision Team, 2004 ▶). Click here for additional data file. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813004686/xu5676sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813004686/xu5676Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Zn(N3)2(C7H10N2)2]F(000) = 816
Mr = 393.79Dx = 1.431 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4302 reflections
a = 14.819 (5) Åθ = 2.7–27.8°
b = 9.610 (5) ŵ = 1.36 mm−1
c = 14.555 (5) ÅT = 293 K
β = 118.158 (5)°Prism, colourless
V = 1827.5 (13) Å30.3 × 0.2 × 0.2 mm
Z = 4
Nonius KappaCCD diffractometer3323 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.019
Graphite monochromatorθmax = 27.8°, θmin = 2.7°
φ scansh = −18→19
15768 measured reflectionsk = −12→12
4302 independent reflectionsl = −19→17
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.033w = 1/[σ2(Fo2) + (0.0512P)2 + 0.563P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.098(Δ/σ)max = 0.006
S = 1.03Δρmax = 0.31 e Å−3
4302 reflectionsΔρmin = −0.45 e Å−3
230 parameters
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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.
xyzUiso*/Ueq
Zn0.71191 (2)−0.27848 (3)0.61121 (2)0.0523 (1)
N1A0.77350 (13)−0.40503 (19)0.73790 (13)0.0500 (5)
N1B0.69230 (13)−0.40145 (19)0.49076 (13)0.0504 (5)
N2A0.89709 (15)−0.6937 (2)0.98096 (15)0.0595 (6)
N2B0.64450 (14)−0.6645 (2)0.24262 (14)0.0571 (6)
N30.57850 (19)−0.2334 (3)0.5965 (2)0.0873 (10)
N40.52367 (14)−0.1422 (2)0.59095 (14)0.0545 (6)
N50.4650 (2)−0.0614 (3)0.5847 (2)0.0865 (10)
N60.81913 (18)−0.1468 (2)0.62440 (17)0.0693 (8)
N70.87832 (14)−0.0916 (2)0.70190 (16)0.0531 (6)
N80.93719 (16)−0.0315 (3)0.77445 (17)0.0734 (8)
C1A0.9886 (2)−0.7725 (3)0.9999 (2)0.0752 (10)
C1B0.7054 (2)−0.6558 (3)0.1887 (2)0.0721 (9)
C2A0.8539 (2)−0.7179 (3)1.05133 (19)0.0660 (9)
C2B0.5557 (2)−0.7569 (3)0.1963 (2)0.0751 (9)
C3A0.85764 (15)−0.5982 (2)0.90434 (15)0.0475 (6)
C3B0.66005 (15)−0.5783 (2)0.32121 (15)0.0470 (6)
C4A0.90324 (17)−0.5695 (3)0.84037 (18)0.0570 (7)
C4B0.73862 (17)−0.4775 (2)0.36129 (17)0.0557 (7)
C5A0.85983 (17)−0.4761 (3)0.76167 (18)0.0583 (8)
C5B0.75054 (17)−0.3949 (3)0.44220 (17)0.0565 (7)
C6A0.73042 (16)−0.4308 (2)0.80006 (16)0.0515 (7)
C6B0.61798 (16)−0.4982 (2)0.45299 (18)0.0535 (7)
C7A0.76869 (16)−0.5216 (2)0.88114 (16)0.0511 (7)
C7B0.59908 (16)−0.5840 (2)0.37233 (18)0.0541 (7)
H1A20.97840−0.815740.936250.1128*
H1A11.00122−0.842741.051440.1128*
H1A31.04621−0.710701.024380.1128*
H1B10.68314−0.577740.142030.1081*
H4A0.96322−0.614890.852250.0684*
H4B0.78234−0.467480.332310.0668*
H1B20.69720−0.739740.149720.1081*
H5A0.89213−0.459920.721250.0699*
H5B0.80265−0.328980.465800.0677*
H1B30.77621−0.644260.238630.1081*
H6A0.67072−0.383240.786340.0618*
H6B0.57653−0.506710.484720.0642*
H2A10.86978−0.640531.098190.0990*
H7A0.73584−0.533120.921530.0613*
H7B0.54548−0.647500.350140.0650*
H2A20.88255−0.801391.090570.0990*
H2A30.78097−0.727651.011510.0990*
H2B10.55497−0.815350.249400.1128*
H2B20.55951−0.813630.143960.1128*
H2B30.49417−0.702230.165010.1128*
U11U22U33U12U13U23
Zn0.0535 (2)0.0544 (2)0.0550 (2)0.0003 (1)0.0306 (1)0.0062 (1)
N1A0.0505 (9)0.0562 (10)0.0507 (9)0.0035 (8)0.0299 (8)0.0048 (8)
N1B0.0488 (9)0.0563 (10)0.0493 (9)−0.0028 (8)0.0259 (8)0.0053 (8)
N2A0.0636 (11)0.0677 (12)0.0524 (10)0.0111 (9)0.0316 (9)0.0107 (9)
N2B0.0592 (11)0.0567 (10)0.0543 (10)−0.0101 (9)0.0260 (9)−0.0023 (9)
N30.0676 (14)0.0791 (15)0.133 (2)0.0182 (12)0.0619 (16)0.0337 (15)
N40.0539 (10)0.0610 (11)0.0555 (10)−0.0035 (9)0.0315 (9)0.0063 (9)
N50.0932 (17)0.0744 (15)0.119 (2)0.0149 (14)0.0724 (16)0.0096 (14)
N60.0831 (14)0.0720 (14)0.0663 (13)−0.0223 (12)0.0464 (12)−0.0047 (11)
N70.0517 (10)0.0619 (11)0.0593 (11)0.0050 (9)0.0374 (10)0.0141 (9)
N80.0582 (12)0.1026 (17)0.0617 (12)−0.0082 (12)0.0301 (10)0.0011 (12)
C1A0.0760 (17)0.0805 (17)0.0680 (16)0.0282 (14)0.0331 (14)0.0180 (13)
C1B0.0857 (17)0.0749 (17)0.0660 (15)−0.0100 (14)0.0442 (14)−0.0078 (13)
C2A0.0845 (17)0.0680 (15)0.0526 (13)0.0008 (13)0.0382 (13)0.0065 (11)
C2B0.0756 (17)0.0686 (15)0.0731 (17)−0.0221 (13)0.0284 (14)−0.0147 (13)
C3A0.0468 (10)0.0538 (11)0.0436 (10)0.0001 (9)0.0227 (9)−0.0029 (9)
C3B0.0429 (10)0.0474 (11)0.0465 (10)−0.0017 (8)0.0176 (9)0.0104 (8)
C4A0.0506 (11)0.0679 (14)0.0637 (13)0.0142 (10)0.0362 (10)0.0113 (11)
C4B0.0547 (12)0.0661 (13)0.0554 (12)−0.0146 (11)0.0335 (10)−0.0008 (10)
C5A0.0559 (12)0.0734 (14)0.0602 (13)0.0069 (11)0.0395 (11)0.0087 (11)
C5B0.0521 (11)0.0654 (13)0.0575 (12)−0.0201 (10)0.0305 (10)−0.0037 (10)
C6A0.0484 (11)0.0582 (12)0.0559 (12)0.0064 (9)0.0313 (10)0.0020 (10)
C6B0.0462 (10)0.0581 (12)0.0643 (13)−0.0008 (9)0.0327 (10)0.0113 (10)
C7A0.0530 (11)0.0616 (13)0.0503 (11)0.0022 (10)0.0340 (10)−0.0006 (9)
C7B0.0435 (10)0.0530 (12)0.0670 (13)−0.0089 (9)0.0270 (10)0.0053 (10)
Zn—N1A2.031 (2)C4B—C5B1.361 (3)
Zn—N1B2.018 (2)C6A—C7A1.358 (3)
Zn—N31.935 (3)C6B—C7B1.351 (3)
Zn—N61.969 (3)C1A—H1A20.9600
N1A—C5A1.344 (4)C1A—H1A10.9600
N1A—C6A1.354 (3)C1A—H1A30.9600
N1B—C5B1.351 (3)C1B—H1B10.9600
N1B—C6B1.345 (3)C1B—H1B20.9600
N2A—C1A1.461 (4)C1B—H1B30.9600
N2A—C2A1.460 (4)C2A—H2A10.9600
N2A—C3A1.346 (3)C2A—H2A20.9600
N2B—C1B1.451 (4)C2A—H2A30.9600
N2B—C2B1.462 (4)C2B—H2B10.9600
N2B—C3B1.341 (3)C2B—H2B20.9600
N3—N41.172 (4)C2B—H2B30.9600
N4—N51.137 (4)C4A—H4A0.9300
N6—N71.179 (3)C4B—H4B0.9300
N7—N81.158 (3)C5A—H5A0.9300
C3A—C4A1.412 (4)C5B—H5B0.9300
C3A—C7A1.405 (3)C6A—H6A0.9300
C3B—C4B1.412 (3)C6B—H6B0.9300
C3B—C7B1.417 (4)C7A—H7A0.9300
C4A—C5A1.355 (4)C7B—H7B0.9300
Zn···H1B1i3.5000C7B···H2B32.9000
N1A···N1B3.210 (3)C7B···H2B12.7300
N1A···N33.113 (4)C7B···H2A3xi3.0800
N1A···N63.225 (3)H1A2···C4A2.7100
N1B···N1A3.210 (3)H1A2···H4A2.2400
N1B···N33.205 (4)H1A1···H2A22.1300
N1B···N63.139 (3)H1A1···N8vii2.5600
N3···N1A3.113 (4)H1A3···C4A2.8500
N3···N1B3.205 (4)H1A3···H4A2.3900
N3···C6A3.339 (4)H1A3···H5Bix2.4500
N3···C7Bii3.367 (4)H1B1···C4B3.0500
N4···N5iii3.286 (4)H1B1···Znvi3.5000
N4···C7Bii3.382 (4)H4A···C1A2.5100
N5···C2Bi3.427 (4)H4A···H1A22.2400
N5···N4iii3.286 (4)H4A···H1A32.3900
N6···N1B3.139 (3)H4A···N7ix2.8200
N6···C5B3.348 (4)H4B···C1B2.5900
N6···N1A3.225 (3)H4B···H1B32.1500
N7···C1Bi3.434 (4)H4B···N7vi2.9100
N8···C5Aiv3.332 (4)H4B···N8vi2.7900
N3···H6A2.8300H1B2···H2B22.1200
N3···H7Bii2.5800H5A···N8ix2.5900
N4···H7Bii2.5900H5B···N62.8100
N5···H2B1ii2.8300H5B···C1Aiv2.9400
N5···H7Av2.9500H5B···H1A3iv2.4500
N5···H2B3i2.7400H1B3···C4B2.6500
N6···H2A1vi2.9300H1B3···H4B2.1500
N6···H5B2.8100H1B3···N7vi2.9100
N7···H4Aiv2.8200H1B3···N8vi2.7600
N7···H1B3i2.9100H6A···N32.8300
N7···H2A1vi2.6600H6B···H6Bii2.5100
N7···H4Bi2.9100H2A1···C7A3.0100
N8···H5Aiv2.5900H2A1···N6i2.9300
N8···H1A1vii2.5600H2A1···N7i2.6600
N8···H2A2vii2.9400H2A1···N8i2.8100
N8···H4Bi2.7900H7A···C2A2.5800
N8···H1B3i2.7600H7A···H2A32.2000
N8···H2A1vi2.8100H7A···N5xii2.9500
C1B···N7vi3.434 (4)H7B···C2B2.5400
C2B···N5vi3.427 (4)H7B···H2B12.2300
C2B···C6Bviii3.383 (4)H7B···H2B32.4900
C5A···N8ix3.332 (4)H7B···N3ii2.5800
C6B···C2Bx3.383 (4)H7B···N4ii2.5900
C7B···N3ii3.367 (4)H2A2···H1A12.1300
C7B···N4ii3.382 (4)H2A2···N8vii2.9400
C1A···H5Bix2.9400H2A3···C7A2.6900
C1A···H4A2.5100H2A3···H7A2.2000
C1B···H4B2.5900H2A3···C7Bxiii3.0800
C2A···H7A2.5800H2B1···C7B2.7300
C2B···H7B2.5400H2B1···H7B2.2300
C4A···H1A22.7100H2B1···N5ii2.8300
C4A···H1A32.8500H2B2···H1B22.1200
C4B···H1B32.6500H2B2···C6Bviii2.9200
C4B···H1B13.0500H2B3···C7B2.9000
C6B···H2B2x2.9200H2B3···H7B2.4900
C7A···H2A13.0100H2B3···N5vi2.7400
C7A···H2A32.6900
N1A—Zn—N1B104.89 (7)N2A—C1A—H1A3109.00
N1A—Zn—N3103.45 (10)H1A2—C1A—H1A1109.00
N1A—Zn—N6107.47 (9)H1A2—C1A—H1A3109.00
N1B—Zn—N3108.32 (10)H1A1—C1A—H1A3110.00
N1B—Zn—N6103.88 (9)N2B—C1B—H1B1110.00
N3—Zn—N6127.05 (11)N2B—C1B—H1B2109.00
Zn—N1A—C5A120.24 (16)N2B—C1B—H1B3109.00
Zn—N1A—C6A124.39 (16)H1B1—C1B—H1B2109.00
C5A—N1A—C6A115.28 (19)H1B1—C1B—H1B3109.00
Zn—N1B—C5B124.17 (16)H1B2—C1B—H1B3109.00
Zn—N1B—C6B120.96 (16)N2A—C2A—H2A1109.00
C5B—N1B—C6B114.9 (2)N2A—C2A—H2A2109.00
C1A—N2A—C2A117.4 (2)N2A—C2A—H2A3109.00
C1A—N2A—C3A120.7 (2)H2A1—C2A—H2A2109.00
C2A—N2A—C3A121.8 (2)H2A1—C2A—H2A3109.00
C1B—N2B—C2B116.1 (2)H2A2—C2A—H2A3109.00
C1B—N2B—C3B121.7 (2)N2B—C2B—H2B1110.00
C2B—N2B—C3B121.6 (2)N2B—C2B—H2B2109.00
Zn—N3—N4144.5 (2)N2B—C2B—H2B3109.00
N3—N4—N5174.7 (3)H2B1—C2B—H2B2110.00
Zn—N6—N7125.8 (2)H2B1—C2B—H2B3109.00
N6—N7—N8176.0 (3)H2B2—C2B—H2B3109.00
N2A—C3A—C4A121.6 (2)C3A—C4A—H4A120.00
N2A—C3A—C7A123.2 (2)C5A—C4A—H4A120.00
C4A—C3A—C7A115.21 (19)C3B—C4B—H4B120.00
N2B—C3B—C4B123.5 (2)C5B—C4B—H4B120.00
N2B—C3B—C7B121.9 (2)N1A—C5A—H5A118.00
C4B—C3B—C7B114.55 (19)C4A—C5A—H5A118.00
C3A—C4A—C5A120.2 (2)N1B—C5B—H5B118.00
C3B—C4B—C5B120.2 (2)C4B—C5B—H5B118.00
N1A—C5A—C4A124.7 (2)N1A—C6A—H6A118.00
N1B—C5B—C4B124.9 (2)C7A—C6A—H6A118.00
N1A—C6A—C7A124.3 (2)N1B—C6B—H6B118.00
N1B—C6B—C7B124.8 (2)C7B—C6B—H6B118.00
C3A—C7A—C6A120.4 (2)C3A—C7A—H7A120.00
C3B—C7B—C6B120.7 (2)C6A—C7A—H7A120.00
N2A—C1A—H1A2109.00C3B—C7B—H7B120.00
N2A—C1A—H1A1109.00C6B—C7B—H7B120.00
N1B—Zn—N1A—C5A55.4 (2)C6B—N1B—C5B—C4B−0.3 (3)
N1B—Zn—N1A—C6A−120.80 (17)Zn—N1B—C6B—C7B179.51 (18)
N3—Zn—N1A—C5A168.85 (19)C5B—N1B—C6B—C7B−0.6 (3)
N3—Zn—N1A—C6A−7.35 (19)C1A—N2A—C3A—C4A−0.6 (3)
N6—Zn—N1A—C5A−54.7 (2)C1A—N2A—C3A—C7A178.6 (2)
N6—Zn—N1A—C6A129.09 (17)C2A—N2A—C3A—C4A176.3 (2)
N1A—Zn—N1B—C5B−107.05 (19)C2A—N2A—C3A—C7A−4.5 (3)
N1A—Zn—N1B—C6B72.84 (18)C1B—N2B—C3B—C4B−3.1 (3)
N3—Zn—N1B—C5B143.0 (2)C1B—N2B—C3B—C7B178.3 (2)
N3—Zn—N1B—C6B−37.13 (19)C2B—N2B—C3B—C4B−173.3 (2)
N6—Zn—N1B—C5B5.6 (2)C2B—N2B—C3B—C7B8.1 (3)
N6—Zn—N1B—C6B−174.48 (17)N2A—C3A—C4A—C5A177.8 (2)
N1A—Zn—N3—N4124.7 (4)C7A—C3A—C4A—C5A−1.5 (3)
N1B—Zn—N3—N4−124.4 (3)N2A—C3A—C7A—C6A−177.3 (2)
N6—Zn—N3—N40.1 (4)C4A—C3A—C7A—C6A2.0 (3)
N1A—Zn—N6—N7−40.6 (3)N2B—C3B—C4B—C5B−179.1 (2)
N1B—Zn—N6—N7−151.4 (2)C7B—C3B—C4B—C5B−0.4 (3)
N3—Zn—N6—N782.3 (3)N2B—C3B—C7B—C6B178.4 (2)
Zn—N1A—C5A—C4A−175.6 (2)C4B—C3B—C7B—C6B−0.4 (3)
C6A—N1A—C5A—C4A0.9 (4)C3A—C4A—C5A—N1A0.0 (4)
Zn—N1A—C6A—C7A176.03 (16)C3B—C4B—C5B—N1B0.8 (4)
C5A—N1A—C6A—C7A−0.3 (3)N1A—C6A—C7A—C3A−1.1 (3)
Zn—N1B—C5B—C4B179.65 (19)N1B—C6B—C7B—C3B0.9 (4)
D—H···AD—HH···AD···AD—H···A
C1A—H1A1···N8vii0.96002.56003.484 (4)163.00
C5A—H5A···N8ix0.93002.59003.332 (4)137.00
C7B—H7B···N3ii0.93002.58003.367 (4)143.00
C7B—H7B···N4ii0.93002.59003.382 (4)143.00
Table 1

Selected bond lengths (Å)

Zn—N1A 2.031 (2)
Zn—N1B 2.018 (2)
Zn—N31.935 (3)
Zn—N61.969 (3)
Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C1A—H1A1⋯N8i 0.962.563.484 (4)163
C5A—H5A⋯N8ii 0.932.593.332 (4)137
C7B—H7B⋯N3iii 0.932.583.367 (4)143
C7B—H7B⋯N4iii 0.932.593.382 (4)143

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

  3 in total

Review 1.  Enantioselective nucleophilic catalysis with "Planar-Chiral" heterocycles.

Authors:  G C Fu
Journal:  Acc Chem Res       Date:  2000-06       Impact factor: 22.384

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  Luminescence ranging from red to blue: a series of copper(I)-halide complexes having rhombic {Cu2(mu-X)2} (X = Br and I) units with N-heteroaromatic ligands.

Authors:  Hiromi Araki; Kiyoshi Tsuge; Yoichi Sasaki; Shoji Ishizaka; Noboru Kitamura
Journal:  Inorg Chem       Date:  2005-12-26       Impact factor: 5.165
  3 in total

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