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The tetra­dentate Schiff base ligand derived from the condensation of 3,5-dibromo­salicylaldehyde and 1,2-phenyl­enediamine, in the presence of pyridine, forms a square-pyramidal five-coordinate Zn complex, [Zn(C20H10Br4N2O2)(C5H5N)]·C3H7N0.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805018787/br6198sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805018787/br6198Isup2.hkl
Contains datablock I

CCDC reference: 277199

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.045
  • wR factor = 0.162
  • Data-to-parameter ratio = 16.0

checkCIF/PLATON results

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Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N4 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2001); program(s) used to refine structure: SHELXL97 (Sheldrick, 2001); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

Pyridine{4,4',6,6'-tetrabromo-2,2'-[1,2- phenylenebis(nitrilomethylidyne)]diphenolato}zinc(II) dimethylformamide solvate top
Crystal data top
[Zn(C20H10Br4N2O2)(C5H5N)]·C3H7N0F(000) = 1648
Mr = 847.51Dx = 1.892 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3507 reflections
a = 8.2289 (9) Åθ = 2.5–22.7°
b = 15.2809 (17) ŵ = 6.23 mm1
c = 23.793 (3) ÅT = 292 K
β = 95.946 (2)°Block, yellow
V = 2975.7 (6) Å30.20 × 0.20 × 0.18 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
5823 independent reflections
Radiation source: fine-focus sealed tube3982 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
φ and ω scansθmax = 26.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 109
Tmin = 0.300, Tmax = 0.326k = 1818
15973 measured reflectionsl = 2629
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0926P)2]
where P = (Fo2 + 2Fc2)/3
5823 reflections(Δ/σ)max = 0.002
363 parametersΔρmax = 0.72 e Å3
0 restraintsΔρmin = 0.83 e Å3
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
xyzUiso*/Ueq
Zn10.06400 (7)0.99760 (4)0.24197 (3)0.03503 (19)
Br40.36814 (8)1.27491 (5)0.26138 (3)0.0579 (2)
Br10.31966 (10)1.00646 (5)0.43821 (3)0.0657 (2)
Br30.11034 (13)1.37468 (5)0.04282 (3)0.0819 (3)
Br20.49434 (11)0.65040 (5)0.42411 (3)0.0756 (3)
N10.0754 (5)0.8631 (3)0.22384 (19)0.0363 (10)
N20.0021 (6)0.9941 (3)0.15314 (19)0.0405 (11)
N30.1608 (5)1.0261 (3)0.2705 (2)0.0398 (11)
N40.3378 (8)0.8600 (5)0.0802 (3)0.0713 (17)
O10.1804 (5)0.9734 (3)0.31802 (16)0.0435 (10)
O20.1701 (5)1.1122 (3)0.23234 (16)0.0439 (10)
O30.2215 (13)0.9618 (9)0.0255 (4)0.199 (6)
C10.2398 (6)0.9021 (4)0.3396 (2)0.0391 (13)
C20.3181 (7)0.9013 (4)0.3961 (2)0.0463 (15)
C30.3929 (7)0.8298 (4)0.4209 (3)0.0520 (16)
H30.44630.83340.45730.062*
C40.3884 (7)0.7509 (4)0.3911 (3)0.0492 (16)
C50.3099 (8)0.7468 (4)0.3374 (3)0.0482 (15)
H50.30630.69390.31790.058*
C60.2348 (7)0.8211 (4)0.3112 (2)0.0385 (13)
C70.1540 (7)0.8068 (4)0.2555 (2)0.0455 (14)
H70.15960.75050.24090.055*
C80.0066 (7)0.8413 (4)0.1702 (2)0.0402 (13)
C90.0498 (9)0.7553 (4)0.1545 (3)0.0532 (16)
H90.02310.70870.17880.064*
C100.1330 (9)0.7415 (4)0.1017 (3)0.0599 (18)
H100.16130.68470.09060.072*
C110.1749 (9)0.8092 (5)0.0653 (3)0.0635 (19)
H110.23140.79830.03010.076*
C120.1330 (8)0.8928 (5)0.0812 (3)0.0566 (17)
H120.16140.93860.05640.068*
C130.0486 (7)0.9109 (4)0.1338 (2)0.0418 (13)
C140.0101 (7)1.0598 (4)0.1196 (2)0.0392 (13)
H140.02841.05130.08190.047*
C150.0733 (7)1.1456 (4)0.1353 (3)0.0409 (13)
C160.0600 (8)1.2094 (4)0.0928 (3)0.0485 (15)
H160.00101.19700.05830.058*
C170.1305 (8)1.2878 (4)0.1010 (3)0.0533 (17)
C180.2219 (8)1.3078 (4)0.1511 (3)0.0566 (17)
H180.27391.36170.15600.068*
C190.2349 (7)1.2469 (4)0.1935 (2)0.0399 (13)
C200.1580 (6)1.1636 (4)0.1897 (2)0.0377 (13)
C210.1717 (7)1.0396 (4)0.3254 (3)0.0466 (14)
H210.07681.03850.35020.056*
C220.3201 (9)1.0553 (4)0.3468 (3)0.0614 (19)
H220.32471.06180.38540.074*
C230.4593 (9)1.0608 (5)0.3100 (4)0.068 (2)
H230.55951.07280.32320.081*
C240.4485 (8)1.0485 (5)0.2536 (4)0.066 (2)
H240.54141.05200.22790.080*
C250.2979 (7)1.0308 (4)0.2353 (3)0.0514 (16)
H250.29181.02180.19690.062*
C260.3520 (16)0.7689 (7)0.0880 (6)0.144 (5)
H26A0.30830.75280.12240.215*
H26B0.46500.75240.09020.215*
H26C0.29230.73940.05670.215*
C270.4172 (14)0.9096 (9)0.1232 (5)0.133 (4)
H27A0.53300.90670.12110.199*
H27B0.39230.88720.15900.199*
H27C0.38150.96930.11930.199*
C280.2523 (14)0.8949 (12)0.0389 (5)0.149 (7)
H280.20410.85360.01380.179*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0366 (3)0.0340 (4)0.0344 (4)0.0009 (3)0.0032 (3)0.0004 (3)
Br40.0640 (4)0.0531 (4)0.0567 (4)0.0161 (3)0.0069 (3)0.0110 (3)
Br10.0848 (5)0.0630 (5)0.0458 (4)0.0135 (4)0.0103 (4)0.0110 (3)
Br30.1443 (8)0.0469 (4)0.0567 (5)0.0017 (5)0.0201 (5)0.0163 (4)
Br20.0937 (6)0.0608 (5)0.0715 (5)0.0280 (4)0.0045 (4)0.0255 (4)
N10.041 (3)0.031 (3)0.038 (3)0.001 (2)0.008 (2)0.004 (2)
N20.039 (3)0.052 (3)0.030 (3)0.006 (2)0.003 (2)0.001 (2)
N30.037 (3)0.032 (3)0.051 (3)0.0065 (19)0.008 (2)0.000 (2)
N40.071 (4)0.076 (5)0.066 (4)0.002 (3)0.001 (3)0.013 (4)
O10.052 (2)0.037 (2)0.040 (2)0.0061 (18)0.0061 (18)0.0038 (18)
O20.047 (2)0.044 (2)0.040 (2)0.0071 (18)0.0002 (18)0.0049 (19)
O30.181 (9)0.298 (14)0.131 (7)0.134 (9)0.072 (7)0.136 (9)
C10.032 (3)0.050 (4)0.035 (3)0.008 (2)0.003 (2)0.004 (3)
C20.042 (3)0.056 (4)0.041 (3)0.009 (3)0.006 (3)0.003 (3)
C30.054 (4)0.059 (4)0.043 (4)0.015 (3)0.003 (3)0.008 (3)
C40.054 (4)0.047 (4)0.048 (4)0.018 (3)0.011 (3)0.017 (3)
C50.062 (4)0.034 (3)0.050 (4)0.012 (3)0.016 (3)0.000 (3)
C60.042 (3)0.035 (3)0.040 (3)0.006 (2)0.009 (2)0.007 (3)
C70.055 (4)0.046 (4)0.036 (3)0.004 (3)0.009 (3)0.002 (3)
C80.047 (3)0.039 (3)0.035 (3)0.006 (3)0.008 (3)0.005 (3)
C90.077 (4)0.026 (3)0.057 (4)0.010 (3)0.007 (3)0.006 (3)
C100.092 (5)0.033 (3)0.053 (4)0.022 (3)0.003 (4)0.012 (3)
C110.078 (5)0.063 (5)0.047 (4)0.024 (4)0.005 (3)0.012 (4)
C120.068 (4)0.062 (5)0.038 (4)0.015 (3)0.001 (3)0.001 (3)
C130.045 (3)0.045 (4)0.036 (3)0.006 (3)0.006 (3)0.006 (3)
C140.046 (3)0.035 (3)0.036 (3)0.004 (2)0.000 (2)0.001 (3)
C150.046 (3)0.033 (3)0.045 (3)0.002 (2)0.009 (3)0.003 (3)
C160.058 (4)0.049 (4)0.039 (3)0.004 (3)0.009 (3)0.007 (3)
C170.075 (4)0.044 (4)0.044 (4)0.004 (3)0.021 (3)0.012 (3)
C180.070 (4)0.044 (4)0.061 (4)0.005 (3)0.029 (4)0.004 (3)
C190.048 (3)0.031 (3)0.042 (3)0.001 (2)0.009 (3)0.003 (3)
C200.039 (3)0.032 (3)0.044 (3)0.001 (2)0.015 (3)0.002 (3)
C210.051 (4)0.037 (3)0.053 (4)0.006 (3)0.010 (3)0.005 (3)
C220.076 (5)0.044 (4)0.070 (5)0.004 (3)0.037 (4)0.000 (3)
C230.051 (4)0.051 (4)0.106 (6)0.010 (3)0.032 (4)0.005 (4)
C240.041 (4)0.060 (5)0.097 (6)0.004 (3)0.004 (4)0.004 (4)
C250.040 (3)0.045 (4)0.069 (4)0.003 (3)0.004 (3)0.002 (3)
C260.140 (10)0.086 (8)0.215 (15)0.017 (7)0.070 (10)0.008 (9)
C270.109 (8)0.161 (12)0.127 (10)0.003 (8)0.002 (7)0.027 (9)
C280.102 (8)0.28 (2)0.068 (7)0.068 (11)0.009 (6)0.050 (10)
Geometric parameters (Å, º) top
Zn1—O21.980 (4)C9—H90.9300
Zn1—O11.993 (4)C10—C111.369 (10)
Zn1—N32.082 (4)C10—H100.9300
Zn1—N12.104 (4)C11—C121.367 (10)
Zn1—N22.123 (5)C11—H110.9300
Br4—C191.904 (6)C12—C131.395 (8)
Br1—C21.893 (6)C12—H120.9300
Br3—C171.913 (6)C14—C151.444 (8)
Br2—C41.895 (6)C14—H140.9300
N1—C71.275 (7)C15—C161.400 (8)
N1—C81.420 (7)C15—C201.434 (8)
N2—C141.289 (7)C16—C171.337 (9)
N2—C131.401 (7)C16—H160.9300
N3—C211.333 (7)C17—C181.376 (9)
N3—C251.336 (7)C18—C191.368 (8)
N4—C281.266 (11)C18—H180.9300
N4—C271.381 (12)C19—C201.420 (8)
N4—C261.407 (12)C21—C221.391 (9)
O1—C11.279 (7)C21—H210.9300
O2—C201.278 (6)C22—C231.369 (10)
O3—C281.093 (17)C22—H220.9300
C1—C61.410 (8)C23—C241.367 (10)
C1—C21.430 (8)C23—H230.9300
C2—C31.358 (8)C24—C251.383 (9)
C3—C41.399 (9)C24—H240.9300
C3—H30.9300C25—H250.9300
C4—C51.373 (9)C26—H26A0.9600
C5—C61.406 (8)C26—H26B0.9600
C5—H50.9300C26—H26C0.9600
C6—C71.436 (8)C27—H27A0.9600
C7—H70.9300C27—H27B0.9600
C8—C131.393 (8)C27—H27C0.9600
C8—C91.402 (8)C28—H280.9300
C9—C101.382 (9)
O2—Zn1—O195.34 (16)C11—C12—C13121.4 (7)
O2—Zn1—N3105.65 (18)C11—C12—H12119.3
O1—Zn1—N395.87 (18)C13—C12—H12119.3
O2—Zn1—N1144.13 (17)C8—C13—C12118.4 (6)
O1—Zn1—N188.70 (17)C8—C13—N2116.2 (5)
N3—Zn1—N1109.37 (18)C12—C13—N2125.3 (6)
O2—Zn1—N288.31 (17)N2—C14—C15126.0 (5)
O1—Zn1—N2160.50 (18)N2—C14—H14117.0
N3—Zn1—N2101.58 (18)C15—C14—H14117.0
N1—Zn1—N277.42 (18)C16—C15—C20120.8 (5)
C7—N1—C8122.4 (5)C16—C15—C14116.6 (5)
C7—N1—Zn1124.7 (4)C20—C15—C14122.4 (5)
C8—N1—Zn1112.8 (4)C17—C16—C15121.3 (6)
C14—N2—C13122.5 (5)C17—C16—H16119.4
C14—N2—Zn1125.0 (4)C15—C16—H16119.4
C13—N2—Zn1112.5 (4)C16—C17—C18121.0 (6)
C21—N3—C25117.9 (5)C16—C17—Br3120.9 (5)
C21—N3—Zn1120.3 (4)C18—C17—Br3118.1 (5)
C25—N3—Zn1121.8 (4)C19—C18—C17118.8 (6)
C28—N4—C27121.7 (11)C19—C18—H18120.6
C28—N4—C26123.5 (12)C17—C18—H18120.6
C27—N4—C26114.7 (10)C18—C19—C20124.2 (6)
C1—O1—Zn1130.6 (4)C18—C19—Br4117.9 (5)
C20—O2—Zn1129.5 (3)C20—C19—Br4117.9 (4)
O1—C1—C6124.3 (5)O2—C20—C19120.3 (5)
O1—C1—C2120.1 (5)O2—C20—C15126.1 (5)
C6—C1—C2115.6 (5)C19—C20—C15113.7 (5)
C3—C2—C1123.7 (6)N3—C21—C22122.4 (6)
C3—C2—Br1118.4 (5)N3—C21—H21118.8
C1—C2—Br1117.9 (5)C22—C21—H21118.8
C2—C3—C4119.1 (6)C23—C22—C21119.0 (7)
C2—C3—H3120.4C23—C22—H22120.5
C4—C3—H3120.4C21—C22—H22120.5
C5—C4—C3119.8 (6)C24—C23—C22118.8 (6)
C5—C4—Br2120.1 (5)C24—C23—H23120.6
C3—C4—Br2120.1 (5)C22—C23—H23120.6
C4—C5—C6121.3 (6)C23—C24—C25119.3 (7)
C4—C5—H5119.4C23—C24—H24120.4
C6—C5—H5119.4C25—C24—H24120.4
C5—C6—C1120.4 (5)N3—C25—C24122.5 (7)
C5—C6—C7115.2 (5)N3—C25—H25118.7
C1—C6—C7124.3 (5)C24—C25—H25118.7
N1—C7—C6126.9 (6)N4—C26—H26A109.5
N1—C7—H7116.6N4—C26—H26B109.5
C6—C7—H7116.6H26A—C26—H26B109.5
C13—C8—C9120.6 (5)N4—C26—H26C109.5
C13—C8—N1116.3 (5)H26A—C26—H26C109.5
C9—C8—N1123.0 (5)H26B—C26—H26C109.5
C10—C9—C8118.3 (6)N4—C27—H27A109.5
C10—C9—H9120.9N4—C27—H27B109.5
C8—C9—H9120.9H27A—C27—H27B109.5
C11—C10—C9121.9 (6)N4—C27—H27C109.5
C11—C10—H10119.1H27A—C27—H27C109.5
C9—C10—H10119.1H27B—C27—H27C109.5
C12—C11—C10119.5 (6)O3—C28—N4135.6 (19)
C12—C11—H11120.3O3—C28—H28112.2
C10—C11—H11120.3N4—C28—H28112.2
O2—Zn1—N1—C790.2 (5)C1—C6—C7—N10.4 (10)
O1—Zn1—N1—C77.2 (5)C7—N1—C8—C13163.0 (5)
N3—Zn1—N1—C7102.9 (5)Zn1—N1—C8—C1313.6 (6)
N2—Zn1—N1—C7159.1 (5)C7—N1—C8—C919.3 (9)
O2—Zn1—N1—C886.3 (4)Zn1—N1—C8—C9164.2 (5)
O1—Zn1—N1—C8176.4 (4)C13—C8—C9—C100.8 (9)
N3—Zn1—N1—C880.6 (4)N1—C8—C9—C10178.5 (6)
N2—Zn1—N1—C817.4 (4)C8—C9—C10—C110.7 (11)
O2—Zn1—N2—C1413.7 (5)C9—C10—C11—C120.4 (12)
O1—Zn1—N2—C14114.9 (6)C10—C11—C12—C130.2 (11)
N3—Zn1—N2—C1492.0 (5)C9—C8—C13—C120.6 (9)
N1—Zn1—N2—C14160.5 (5)N1—C8—C13—C12178.4 (5)
O2—Zn1—N2—C13165.9 (4)C9—C8—C13—N2179.1 (6)
O1—Zn1—N2—C1364.6 (7)N1—C8—C13—N23.1 (7)
N3—Zn1—N2—C1388.5 (4)C11—C12—C13—C80.3 (10)
N1—Zn1—N2—C1319.1 (4)C11—C12—C13—N2178.6 (6)
O2—Zn1—N3—C2184.2 (4)C14—N2—C13—C8161.6 (5)
O1—Zn1—N3—C2113.0 (5)Zn1—N2—C13—C818.0 (6)
N1—Zn1—N3—C21103.7 (4)C14—N2—C13—C1216.8 (9)
N2—Zn1—N3—C21175.7 (4)Zn1—N2—C13—C12163.6 (5)
O2—Zn1—N3—C2596.4 (5)C13—N2—C14—C15174.7 (5)
O1—Zn1—N3—C25166.3 (5)Zn1—N2—C14—C154.9 (8)
N1—Zn1—N3—C2575.6 (5)N2—C14—C15—C16175.7 (6)
N2—Zn1—N3—C254.9 (5)N2—C14—C15—C209.5 (9)
O2—Zn1—O1—C1140.6 (5)C20—C15—C16—C172.4 (9)
N3—Zn1—O1—C1113.0 (5)C14—C15—C16—C17172.5 (6)
N1—Zn1—O1—C13.7 (5)C15—C16—C17—C181.5 (10)
N2—Zn1—O1—C140.5 (8)C15—C16—C17—Br3179.6 (5)
O1—Zn1—O2—C20175.5 (4)C16—C17—C18—C192.3 (10)
N3—Zn1—O2—C2086.9 (5)Br3—C17—C18—C19178.8 (4)
N1—Zn1—O2—C2080.3 (5)C17—C18—C19—C200.9 (9)
N2—Zn1—O2—C2014.7 (5)C17—C18—C19—Br4177.9 (5)
Zn1—O1—C1—C60.7 (8)Zn1—O2—C20—C19174.7 (4)
Zn1—O1—C1—C2179.6 (4)Zn1—O2—C20—C156.4 (8)
O1—C1—C2—C3175.8 (6)C18—C19—C20—O2176.6 (5)
C6—C1—C2—C34.0 (9)Br4—C19—C20—O24.6 (7)
O1—C1—C2—Br13.3 (7)C18—C19—C20—C154.4 (8)
C6—C1—C2—Br1176.9 (4)Br4—C19—C20—C15174.4 (4)
C1—C2—C3—C42.9 (10)C16—C15—C20—O2176.0 (5)
Br1—C2—C3—C4178.0 (5)C14—C15—C20—O29.4 (9)
C2—C3—C4—C50.4 (9)C16—C15—C20—C195.1 (8)
C2—C3—C4—Br2179.1 (5)C14—C15—C20—C19169.6 (5)
C3—C4—C5—C60.7 (9)C25—N3—C21—C222.1 (9)
Br2—C4—C5—C6178.0 (4)Zn1—N3—C21—C22177.3 (5)
C4—C5—C6—C10.5 (9)N3—C21—C22—C232.9 (10)
C4—C5—C6—C7178.6 (6)C21—C22—C23—C241.7 (11)
O1—C1—C6—C5177.1 (5)C22—C23—C24—C250.0 (11)
C2—C1—C6—C52.7 (8)C21—N3—C25—C240.3 (9)
O1—C1—C6—C73.9 (9)Zn1—N3—C25—C24179.1 (5)
C2—C1—C6—C7176.4 (5)C23—C24—C25—N30.8 (11)
C8—N1—C7—C6177.1 (5)C27—N4—C28—O31 (2)
Zn1—N1—C7—C66.8 (9)C26—N4—C28—O3177.6 (15)
C5—C6—C7—N1178.7 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C21—H21···O10.932.533.092 (7)119
C24—H24···O2i0.932.563.275 (8)134
C12—H12···O3ii0.932.483.395 (11)168
Symmetry codes: (i) x1, y, z; (ii) x, y+2, z.
 

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