Literature DB >> 22219797

Dibromido{2-[(4-nitro-phen-yl)imino-meth-yl]pyridine-κN,N'}zinc(II).

Sadegh Salehzadeh, Mehdi Khalaj, Saeed Dehghanpour, Isaac Tarmoradi.   

Abstract

In the title compound, [ZnBr(2)(C(12)H(9)N(3)O(2))], the Zn(II) ion is bonded to two Br ions and two N atoms of the diimine ligand in a distorted tetra-hedral geometry. With the exception of the Br atoms, all other atoms are disordered over two sets of sites corresponding to a 180° rotation of the mol-ecule along [[Formula: see text]02]. The refined occupancies of the components are 0.809 (2) and 0.191 (2). In addition, the crystal studied was a non-merohedral twin with a refined component ratio of 0.343 (2):0.657 (2).

Entities:  

Year:  2011        PMID: 22219797      PMCID: PMC3246977          DOI: 10.1107/S1600536811042231

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


Related literature

For related structures, see: Khalaj et al. (2009 ▶). For background information on diimine complexes, see: Khalaj et al. (2010 ▶); Salehzadeh et al. (2011 ▶).

Experimental

Crystal data

[ZnBr2(C12H9N3O2)] M = 452.41 Triclinic, a = 7.2614 (5) Å b = 7.9228 (8) Å c = 13.6436 (15) Å α = 87.724 (4)° β = 74.719 (6)° γ = 82.007 (6)° V = 749.81 (12) Å3 Z = 2 Mo Kα radiation μ = 6.97 mm−1 T = 150 K 0.28 × 0.15 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T min = 0.417, T max = 0.588 5868 measured reflections 3252 independent reflections 2630 reflections with I > 2σ(I) R int = 0.082

Refinement

R[F 2 > 2σ(F 2)] = 0.056 wR(F 2) = 0.140 S = 1.04 3252 reflections 237 parameters 48 restraints H-atom parameters constrained Δρmax = 0.70 e Å−3 Δρmin = −1.24 e Å−3 Data collection: COLLECT (Nonius, 2002 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811042231/gk2406sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042231/gk2406Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[ZnBr2(C12H9N3O2)]Z = 2
Mr = 452.41F(000) = 436
Triclinic, P1Dx = 2.004 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.2614 (5) ÅCell parameters from 6572 reflections
b = 7.9228 (8) Åθ = 2.6–27.5°
c = 13.6436 (15) ŵ = 6.97 mm1
α = 87.724 (4)°T = 150 K
β = 74.719 (6)°Plate, colourless
γ = 82.007 (6)°0.28 × 0.15 × 0.08 mm
V = 749.81 (12) Å3
Nonius KappaCCD diffractometer3252 independent reflections
Radiation source: fine-focus sealed tube2630 reflections with I > 2σ(I)
graphiteRint = 0.082
Detector resolution: 9 pixels mm-1θmax = 27.6°, θmin = 2.6°
φ scans and ω scans with κ offsetsh = −9→9
Absorption correction: multi-scan (SORTAV; Blessing, 1995)k = −10→10
Tmin = 0.417, Tmax = 0.588l = −9→17
5868 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0564P)2 + 2.802P] where P = (Fo2 + 2Fc2)/3
3252 reflections(Δ/σ)max < 0.001
237 parametersΔρmax = 0.70 e Å3
48 restraintsΔρmin = −1.24 e Å3
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.
xyzUiso*/UeqOcc. (<1)
Br10.33600 (13)0.49862 (12)0.72990 (8)0.0358 (2)
Br20.43682 (13)−0.00007 (12)0.71961 (8)0.0366 (3)
Zn10.20560 (17)0.24153 (16)0.74480 (11)0.0259 (3)0.809 (2)
O10.056 (2)0.137 (2)0.2086 (8)0.036 (3)0.809 (2)
O20.2084 (14)0.3589 (19)0.1962 (8)0.034 (3)0.809 (2)
N1−0.0223 (12)0.2369 (13)0.8687 (7)0.027 (2)0.809 (2)
N2−0.0123 (10)0.2536 (11)0.6714 (6)0.0235 (16)0.809 (2)
N30.1139 (15)0.2531 (18)0.2458 (5)0.027 (2)0.809 (2)
C1−0.0292 (14)0.2250 (15)0.9678 (9)0.032 (2)0.809 (2)
H1A0.08880.21230.98680.038*0.809 (2)
C2−0.2000 (15)0.2302 (17)1.0447 (9)0.036 (3)0.809 (2)
H2A−0.19980.22391.11430.043*0.809 (2)
C3−0.3711 (15)0.245 (2)1.0150 (10)0.038 (3)0.809 (2)
H3A−0.49060.24521.06470.046*0.809 (2)
C4−0.3672 (16)0.259 (2)0.9150 (10)0.042 (3)0.809 (2)
H4A−0.48390.27620.89470.050*0.809 (2)
C5−0.1929 (19)0.249 (2)0.8435 (6)0.029 (2)0.809 (2)
C6−0.1789 (12)0.2637 (12)0.7350 (8)0.027 (2)0.809 (2)
H6A−0.29220.28070.71150.032*0.809 (2)
C70.0079 (12)0.2568 (13)0.5649 (7)0.022 (2)0.809 (2)
C8−0.1213 (16)0.1964 (17)0.5189 (8)0.026 (2)0.809 (2)
H8A−0.23200.15330.56030.032*0.809 (2)
C9−0.091 (2)0.198 (2)0.4148 (11)0.028 (3)0.809 (2)
H9A−0.18010.15970.38370.033*0.809 (2)
C100.074 (3)0.259 (2)0.3573 (6)0.023 (3)0.809 (2)
C110.2013 (19)0.3242 (17)0.3996 (9)0.024 (3)0.809 (2)
H11A0.30710.37310.35750.029*0.809 (2)
C120.1737 (16)0.3183 (16)0.5044 (8)0.027 (2)0.809 (2)
H12A0.26510.35510.53450.032*0.809 (2)
Zn1A−0.4500 (7)0.2540 (7)0.7425 (4)0.0259 (3)0.191 (2)
O1A0.101 (12)0.141 (12)0.196 (3)0.036 (3)0.191 (2)
O2A0.252 (8)0.354 (10)0.211 (3)0.034 (3)0.191 (2)
N1A−0.349 (2)0.259 (6)0.8676 (10)0.027 (2)0.191 (2)
N2A−0.1587 (13)0.243 (4)0.6709 (11)0.0235 (16)0.191 (2)
N3A0.156 (7)0.240 (8)0.2468 (11)0.027 (2)0.191 (2)
C1A−0.441 (3)0.265 (6)0.9666 (11)0.032 (2)0.191 (2)
H1AA−0.57780.27180.98500.038*0.191 (2)
C2A−0.348 (4)0.262 (8)1.0440 (14)0.036 (3)0.191 (2)
H2AA−0.41830.27971.11300.043*0.191 (2)
C3A−0.147 (4)0.233 (9)1.0156 (16)0.038 (3)0.191 (2)
H3AA−0.07830.21131.06600.046*0.191 (2)
C4A−0.051 (3)0.234 (10)0.916 (2)0.042 (3)0.191 (2)
H4AA0.08560.22290.89610.050*0.191 (2)
C5A−0.154 (3)0.252 (7)0.8437 (12)0.029 (2)0.191 (2)
C6A−0.0591 (17)0.252 (5)0.7351 (15)0.027 (2)0.191 (2)
H6AA0.07520.25760.71210.032*0.191 (2)
C7A−0.072 (2)0.246 (4)0.5645 (11)0.022 (2)0.191 (2)
C8A0.108 (4)0.298 (7)0.5209 (16)0.026 (2)0.191 (2)
H8AA0.17740.33750.56350.032*0.191 (2)
C9A0.187 (6)0.292 (10)0.4172 (18)0.028 (3)0.191 (2)
H9AA0.30850.32940.38750.033*0.191 (2)
C10A0.083 (8)0.231 (11)0.3581 (11)0.023 (3)0.191 (2)
C11A−0.090 (8)0.169 (11)0.3986 (17)0.024 (3)0.191 (2)
H11B−0.15200.12100.35560.029*0.191 (2)
C12A−0.171 (5)0.178 (8)0.5029 (14)0.027 (2)0.191 (2)
H12B−0.29230.13940.53190.032*0.191 (2)
U11U22U33U12U13U23
Br10.0307 (5)0.0262 (4)0.0540 (6)−0.0087 (3)−0.0146 (5)−0.0002 (5)
Br20.0281 (4)0.0272 (4)0.0537 (7)−0.0054 (3)−0.0079 (5)−0.0030 (5)
Zn10.0226 (5)0.0275 (5)0.0292 (6)−0.0083 (4)−0.0068 (5)−0.0006 (6)
O10.041 (9)0.039 (4)0.031 (5)−0.007 (6)−0.013 (4)−0.010 (4)
O20.037 (7)0.035 (4)0.029 (5)−0.010 (5)−0.009 (4)0.009 (4)
N10.028 (4)0.024 (4)0.031 (5)−0.005 (3)−0.008 (4)0.001 (5)
N20.026 (4)0.016 (4)0.031 (4)−0.004 (3)−0.009 (4)−0.004 (4)
N30.023 (6)0.029 (4)0.031 (4)0.006 (5)−0.013 (4)−0.003 (5)
C10.026 (5)0.032 (5)0.040 (7)−0.001 (4)−0.013 (5)0.003 (6)
C20.042 (6)0.043 (7)0.017 (5)−0.007 (6)0.003 (5)−0.006 (6)
C30.018 (5)0.065 (9)0.028 (7)−0.005 (5)0.002 (5)−0.008 (7)
C40.023 (5)0.060 (8)0.042 (8)−0.010 (5)−0.006 (6)0.012 (8)
C50.026 (6)0.029 (4)0.034 (5)−0.009 (5)−0.008 (5)−0.009 (5)
C60.023 (4)0.023 (5)0.037 (6)−0.006 (4)−0.011 (5)0.001 (5)
C70.020 (6)0.020 (4)0.024 (4)−0.002 (5)−0.002 (4)0.001 (4)
C80.025 (6)0.022 (5)0.030 (6)−0.009 (4)−0.001 (5)0.000 (5)
C90.031 (6)0.019 (8)0.033 (7)−0.004 (5)−0.008 (5)−0.007 (5)
C100.025 (4)0.015 (8)0.027 (4)0.003 (4)−0.006 (4)0.001 (4)
C110.033 (6)0.014 (6)0.021 (6)−0.005 (4)0.001 (5)0.002 (4)
C120.025 (6)0.027 (5)0.029 (6)−0.011 (5)−0.003 (4)−0.001 (5)
Zn1A0.0226 (5)0.0275 (5)0.0292 (6)−0.0083 (4)−0.0068 (5)−0.0006 (6)
O1A0.041 (9)0.039 (4)0.031 (5)−0.007 (6)−0.013 (4)−0.010 (4)
O2A0.037 (7)0.035 (4)0.029 (5)−0.010 (5)−0.009 (4)0.009 (4)
N1A0.028 (4)0.024 (4)0.031 (5)−0.005 (3)−0.008 (4)0.001 (5)
N2A0.026 (4)0.016 (4)0.031 (4)−0.004 (3)−0.009 (4)−0.004 (4)
N3A0.023 (6)0.029 (4)0.031 (4)0.006 (5)−0.013 (4)−0.003 (5)
C1A0.026 (5)0.032 (5)0.040 (7)−0.001 (4)−0.013 (5)0.003 (6)
C2A0.042 (6)0.043 (7)0.017 (5)−0.007 (6)0.003 (5)−0.006 (6)
C3A0.018 (5)0.065 (9)0.028 (7)−0.005 (5)0.002 (5)−0.008 (7)
C4A0.023 (5)0.060 (8)0.042 (8)−0.010 (5)−0.006 (6)0.012 (8)
C5A0.026 (6)0.029 (4)0.034 (5)−0.009 (5)−0.008 (5)−0.009 (5)
C6A0.023 (4)0.023 (5)0.037 (6)−0.006 (4)−0.011 (5)0.001 (5)
C7A0.020 (6)0.020 (4)0.024 (4)−0.002 (5)−0.002 (4)0.001 (4)
C8A0.025 (6)0.022 (5)0.030 (6)−0.009 (4)−0.001 (5)0.000 (5)
C9A0.031 (6)0.019 (8)0.033 (7)−0.004 (5)−0.008 (5)−0.007 (5)
C10A0.025 (4)0.015 (8)0.027 (4)0.003 (4)−0.006 (4)0.001 (4)
C11A0.033 (6)0.014 (6)0.021 (6)−0.005 (4)0.001 (5)0.002 (4)
C12A0.025 (6)0.027 (5)0.029 (6)−0.011 (5)−0.003 (4)−0.001 (5)
Br1—Zn1Ai2.340 (5)C12—H12A0.9500
Br1—Zn12.3428 (14)Zn1A—N1A2.033 (9)
Br2—Zn12.3357 (16)Zn1A—N2A2.074 (8)
Br2—Zn1Ai2.339 (5)Zn1A—Br2ii2.339 (5)
Zn1—N12.034 (9)Zn1A—Br1ii2.340 (5)
Zn1—N22.074 (7)O1A—N3A1.239 (10)
O1—N31.239 (10)O2A—N3A1.226 (10)
O2—N31.226 (10)N1A—C1A1.340 (14)
N1—C11.340 (14)N1A—C5A1.361 (16)
N1—C51.361 (16)N2A—C6A1.284 (11)
N2—C61.284 (11)N2A—C7A1.422 (12)
N2—C71.421 (12)N3A—C10A1.472 (10)
N3—C101.472 (10)C1A—C2A1.394 (14)
C1—C21.394 (14)C1A—H1AA0.9500
C1—H1A0.9500C2A—C3A1.394 (15)
C2—C31.394 (15)C2A—H2AA0.9500
C2—H2A0.9500C3A—C4A1.357 (18)
C3—C41.357 (18)C3A—H3AA0.9500
C3—H3A0.9500C4A—C5A1.373 (16)
C4—C51.373 (16)C4A—H4AA0.9500
C4—H4A0.9500C5A—C6A1.459 (14)
C5—C61.459 (14)C6A—H6AA0.9500
C6—H6A0.9500C7A—C8A1.400 (14)
C7—C81.400 (14)C7A—C12A1.406 (12)
C7—C121.405 (12)C8A—C9A1.379 (18)
C8—C91.379 (18)C8A—H8AA0.9500
C8—H8A0.9500C9A—C10A1.381 (18)
C9—C101.381 (18)C9A—H9AA0.9500
C9—H9A0.9500C10A—C11A1.380 (19)
C10—C111.380 (19)C11A—C12A1.390 (16)
C11—C121.390 (16)C11A—H11B0.9500
C11—H11A0.9500C12A—H12B0.9500
Zn1Ai—Br1—Zn164.77 (11)C7—C12—H12A120.6
Zn1—Br2—Zn1Ai64.90 (12)N1A—Zn1A—N2A81.2 (3)
N1—Zn1—N281.2 (3)N1A—Zn1A—Br2ii114.8 (13)
N1—Zn1—Br2116.1 (3)N2A—Zn1A—Br2ii110.8 (8)
N2—Zn1—Br2118.0 (2)N1A—Zn1A—Br1ii111.9 (12)
N1—Zn1—Br1112.3 (3)N2A—Zn1A—Br1ii120.6 (8)
N2—Zn1—Br1111.5 (2)Br2ii—Zn1A—Br1ii113.73 (19)
Br2—Zn1—Br1113.75 (5)C1A—N1A—C5A116.9 (9)
C1—N1—C5117.0 (8)C1A—N1A—Zn1A130.7 (7)
C1—N1—Zn1130.6 (7)C5A—N1A—Zn1A112.4 (7)
C5—N1—Zn1112.4 (7)C6A—N2A—C7A121.1 (8)
C6—N2—C7121.2 (7)C6A—N2A—Zn1A111.5 (6)
C6—N2—Zn1111.5 (6)C7A—N2A—Zn1A127.0 (6)
C7—N2—Zn1127.2 (5)O2A—N3A—O1A124.4 (8)
O2—N3—O1124.5 (7)O2A—N3A—C10A117.9 (9)
O2—N3—C10118.0 (9)O1A—N3A—C10A117.4 (9)
O1—N3—C10117.5 (9)N1A—C1A—C2A123.4 (10)
N1—C1—C2123.6 (10)N1A—C1A—H1AA118.3
N1—C1—H1A118.2C2A—C1A—H1AA118.3
C2—C1—H1A118.2C1A—C2A—C3A117.0 (12)
C1—C2—C3117.2 (12)C1A—C2A—H2AA121.5
C1—C2—H2A121.4C3A—C2A—H2AA121.5
C3—C2—H2A121.4C4A—C3A—C2A119.8 (12)
C4—C3—C2120.0 (11)C4A—C3A—H3AA120.1
C4—C3—H3A120.0C2A—C3A—H3AA120.1
C2—C3—H3A120.0C3A—C4A—C5A119.3 (11)
C3—C4—C5119.4 (11)C3A—C4A—H4AA120.4
C3—C4—H4A120.3C5A—C4A—H4AA120.4
C5—C4—H4A120.3N1A—C5A—C4A122.7 (10)
N1—C5—C4122.6 (10)N1A—C5A—C6A115.1 (9)
N1—C5—C6115.1 (9)C4A—C5A—C6A122.1 (12)
C4—C5—C6122.1 (11)N2A—C6A—C5A119.5 (9)
N2—C6—C5119.5 (9)N2A—C6A—H6AA120.2
N2—C6—H6A120.2C5A—C6A—H6AA120.2
C5—C6—H6A120.2C8A—C7A—C12A119.9 (9)
C8—C7—C12119.9 (8)C8A—C7A—N2A123.9 (8)
C8—C7—N2123.9 (8)C12A—C7A—N2A116.0 (8)
C12—C7—N2116.1 (8)C9A—C8A—C7A121.2 (10)
C9—C8—C7121.2 (10)C9A—C8A—H8AA119.4
C9—C8—H8A119.4C7A—C8A—H8AA119.4
C7—C8—H8A119.4C8A—C9A—C10A117.6 (12)
C8—C9—C10117.6 (11)C8A—C9A—H9AA121.2
C8—C9—H9A121.2C10A—C9A—H9AA121.2
C10—C9—H9A121.2C11A—C10A—C9A122.9 (9)
C11—C10—C9122.9 (8)C11A—C10A—N3A118.6 (12)
C11—C10—N3118.7 (12)C9A—C10A—N3A118.4 (13)
C9—C10—N3118.4 (13)C10A—C11A—C12A119.5 (10)
C10—C11—C12119.4 (9)C10A—C11A—H11B120.3
C10—C11—H11A120.3C12A—C11A—H11B120.3
C12—C11—H11A120.3C11A—C12A—C7A118.7 (10)
C11—C12—C7118.7 (10)C11A—C12A—H12B120.6
C11—C12—H12A120.6C7A—C12A—H12B120.6
Br1—Zn12.3428 (14)
Br2—Zn12.3357 (16)
Zn1—N12.034 (9)
Zn1—N22.074 (7)
N1—Zn1—N281.2 (3)
N1—Zn1—Br2116.1 (3)
N2—Zn1—Br2118.0 (2)
N1—Zn1—Br1112.3 (3)
N2—Zn1—Br1111.5 (2)
Br2—Zn1—Br1113.75 (5)
  6 in total

1.  A short history of SHELX.

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

2.  An empirical correction for absorption anisotropy.

Authors:  R H Blessing
Journal:  Acta Crystallogr A       Date:  1995-01-01       Impact factor: 2.290

3.  Dibromido{2-[(4-bromo-phen-yl)imino-meth-yl]pyridine-κN,N'}zinc(II).

Authors:  Mehdi Khalaj; Saeed Dehghanpour; Ali Mahmoudi; Shila Seyedidarzam
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-07-11

4.  Bromidotricarbon-yl[4-chloro-N-(2-pyridyl-methyl-idene)aniline-κN,N']rhenium(I).

Authors:  Mehdi Khalaj; Saeed Dehghanpour; Roghaieh Aleeshah; Ali Mahmoudi
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-11-24

5.  Di-μ-chlorido-bis-{chlorido[4-nitro-N-(pyridin-2-yl-methyl-idene-κN)aniline-κN]mercury(II)}.

Authors:  Sadegh Salehzadeh; Saeed Dehghanpour; Mehdi Khalaj; Mohammad Rahimishakiba
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-02-12

6.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  6 in total
  2 in total

1.  [N,N'-Bis(2,6-dichloro-benzyl-idene)propane-1,3-diamine-κ(2)N,N']dibromidozinc.

Authors:  Aliakbar Dehno Khalaji; Gholamhossein Grivani; Mohammad Seyyedi; Karla Fejfarová; Michal Dušek
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-06-23

2.  Dibromido{2-[(4-fluoro-phen-yl)imino-meth-yl]pyridine-κ(2)N,N'}zinc.

Authors:  Saeed Dehghanpour; Ali Mahmoudi
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-07-25
  2 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.