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In the title Schiff base complex, [ZnCl2(C10H12NO2)2], the ZnII ion is in a distorted tetra­hedral ZnO2Cl2 coordination environment.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806047969/xu2153sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806047969/xu2153Isup2.hkl
Contains datablock I

CCDC reference: 630518

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.011 Å
  • R factor = 0.074
  • wR factor = 0.217
  • Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O3 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Zn1 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.38 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 11
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

(I) top
Crystal data top
[Zn(C10H12NO2)2Cl2]F(000) = 1016
Mr = 492.68Dx = 1.545 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2730 reflections
a = 11.547 (3) Åθ = 2.2–25.7°
b = 10.503 (3) ŵ = 1.44 mm1
c = 17.469 (3) ÅT = 298 K
β = 91.000 (3)°Block, yellow
V = 2118.3 (9) Å30.22 × 0.14 × 0.10 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
3729 independent reflections
Radiation source: fine-focus sealed tube2165 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.079
φ and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
h = 1313
Tmin = 0.742, Tmax = 0.869k = 612
10504 measured reflectionsl = 2020
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)] = 0.074Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.217H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.091P)2 + 9.1479P]
where P = (Fo2 + 2Fc2)/3
3729 reflections(Δ/σ)max < 0.001
262 parametersΔρmax = 0.88 e Å3
1 restraintΔρmin = 0.87 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
Zn10.28463 (8)0.75226 (8)0.07673 (5)0.0338 (3)
Cl10.19590 (19)0.7445 (2)0.18916 (12)0.0484 (6)
Cl20.3210 (2)0.5660 (2)0.02217 (15)0.0622 (8)
O10.4166 (4)0.8714 (5)0.0854 (3)0.0441 (15)
H10.40050.94500.07390.066*
O20.6953 (5)0.6426 (5)0.2354 (4)0.0536 (18)
O30.2056 (5)0.8772 (5)0.0112 (3)0.0483 (17)
H30.22160.95040.02400.072*
O40.0334 (5)0.6618 (5)0.1722 (3)0.0475 (16)
N10.4359 (6)1.1161 (6)0.0806 (4)0.0384 (17)
N20.2041 (6)1.1180 (6)0.0115 (4)0.0427 (19)
C10.5891 (8)1.2300 (7)0.1447 (5)0.049 (2)
H1A0.59911.27990.09920.073*
H1B0.66361.21130.16730.073*
H1C0.54361.27690.18050.073*
C20.5291 (7)1.1092 (7)0.1246 (5)0.0324 (19)
C30.5681 (7)0.9851 (7)0.1517 (5)0.0336 (19)
C40.5095 (6)0.8704 (7)0.1315 (5)0.0330 (19)
C50.5527 (7)0.7531 (8)0.1586 (5)0.0364 (18)
H50.51790.67720.14320.044*
C60.6461 (7)0.7517 (8)0.2076 (5)0.0407 (19)
C70.7015 (8)0.8628 (9)0.2302 (5)0.050 (2)
H70.76360.85980.26480.061*
C80.6642 (7)0.9765 (8)0.2015 (5)0.042 (2)
H80.70371.05050.21530.051*
C90.6519 (9)0.5234 (8)0.2058 (6)0.054 (3)
H9A0.57670.50690.22630.081*
H9B0.70390.45590.22040.081*
H9C0.64600.52790.15100.081*
C100.1009 (8)1.2437 (8)0.0844 (5)0.047 (2)
H10A0.09491.30690.04500.071*
H10B0.02741.23470.11040.071*
H10C0.15821.26950.12040.071*
C110.1356 (7)1.1184 (7)0.0492 (5)0.0341 (19)
C120.0966 (6)0.9974 (7)0.0798 (4)0.0304 (17)
C130.1315 (6)0.8795 (7)0.0476 (4)0.0289 (18)
C140.0906 (7)0.7671 (7)0.0804 (5)0.0330 (18)
H140.11640.68920.06140.040*
C150.0144 (7)0.7697 (7)0.1390 (5)0.0353 (19)
C160.0243 (7)0.8847 (7)0.1723 (5)0.041 (2)
H160.07640.88440.21350.049*
C170.0161 (7)0.9959 (8)0.1427 (5)0.039 (2)
H170.00901.07260.16390.047*
C180.0035 (9)0.5411 (8)0.1408 (6)0.054 (3)
H18A0.07710.52470.14880.081*
H18B0.04920.47610.16540.081*
H18C0.01840.54100.08690.081*
C190.3836 (7)1.2317 (7)0.0494 (5)0.042 (2)
H19A0.40531.24160.00360.051*
H19B0.41241.30490.07770.051*
C200.2537 (7)1.2263 (7)0.0545 (5)0.041 (2)
H20A0.23241.21940.10780.049*
H20B0.22101.30480.03440.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0387 (5)0.0176 (4)0.0446 (6)0.0020 (4)0.0161 (4)0.0041 (4)
Cl10.0520 (13)0.0464 (12)0.0465 (13)0.0000 (12)0.0057 (10)0.0099 (11)
Cl20.093 (2)0.0238 (11)0.0693 (17)0.0106 (12)0.0083 (14)0.0042 (11)
O10.034 (3)0.026 (3)0.072 (4)0.007 (3)0.021 (3)0.007 (3)
O20.061 (4)0.032 (3)0.067 (5)0.001 (3)0.029 (3)0.009 (3)
O30.074 (4)0.014 (3)0.055 (4)0.005 (3)0.046 (3)0.003 (2)
O40.047 (4)0.034 (3)0.061 (4)0.001 (3)0.024 (3)0.010 (3)
N10.036 (4)0.019 (3)0.059 (5)0.006 (3)0.014 (4)0.003 (3)
N20.050 (4)0.027 (4)0.049 (4)0.003 (3)0.035 (4)0.005 (3)
C10.062 (6)0.018 (4)0.065 (6)0.014 (4)0.015 (5)0.011 (4)
C20.030 (4)0.024 (4)0.043 (5)0.002 (3)0.003 (4)0.005 (3)
C30.034 (5)0.026 (4)0.041 (5)0.002 (4)0.007 (4)0.003 (4)
C40.024 (4)0.026 (4)0.048 (5)0.003 (3)0.005 (4)0.003 (4)
C50.034 (4)0.032 (4)0.044 (5)0.003 (4)0.003 (4)0.003 (4)
C60.052 (5)0.023 (4)0.047 (5)0.005 (4)0.008 (4)0.005 (4)
C70.046 (6)0.049 (6)0.056 (6)0.005 (5)0.020 (5)0.004 (5)
C80.044 (5)0.031 (5)0.052 (6)0.006 (4)0.011 (4)0.000 (4)
C90.068 (7)0.029 (5)0.064 (7)0.007 (5)0.012 (5)0.009 (4)
C100.049 (5)0.032 (5)0.059 (6)0.003 (5)0.011 (4)0.007 (5)
C110.034 (5)0.023 (4)0.044 (5)0.000 (4)0.005 (4)0.009 (4)
C120.032 (4)0.029 (4)0.030 (4)0.003 (4)0.008 (3)0.002 (3)
C130.025 (4)0.030 (4)0.031 (4)0.003 (3)0.012 (3)0.004 (3)
C140.038 (4)0.019 (4)0.042 (5)0.005 (4)0.003 (4)0.001 (4)
C150.031 (4)0.026 (4)0.049 (5)0.001 (3)0.002 (4)0.004 (4)
C160.046 (5)0.033 (5)0.044 (5)0.005 (4)0.020 (4)0.008 (4)
C170.032 (5)0.033 (5)0.053 (5)0.001 (4)0.011 (4)0.016 (4)
C180.065 (7)0.032 (5)0.064 (6)0.000 (5)0.022 (5)0.015 (5)
C190.045 (5)0.016 (4)0.065 (6)0.003 (4)0.016 (4)0.006 (4)
C200.047 (5)0.017 (4)0.059 (5)0.004 (3)0.013 (4)0.012 (4)
Geometric parameters (Å, º) top
Zn1—O11.975 (5)C7—H70.9300
Zn1—O31.957 (5)C8—H80.9300
Zn1—Cl12.233 (2)C9—H9A0.9600
Zn1—Cl22.219 (2)C9—H9B0.9600
O1—C41.330 (9)C9—H9C0.9600
O1—H10.8200C10—C111.505 (10)
O2—C61.364 (9)C10—H10A0.9600
O2—C91.442 (10)C10—H10B0.9600
O3—C131.326 (8)C10—H10C0.9600
O3—H30.8200C11—C121.448 (10)
O4—C151.383 (9)C12—C131.415 (10)
O4—C181.422 (10)C12—C171.427 (11)
N1—C21.313 (10)C13—C141.392 (10)
N1—C191.457 (9)C14—C151.338 (11)
N2—C111.312 (10)C14—H140.9300
N2—C201.472 (9)C15—C161.411 (11)
C1—C21.485 (9)C16—C171.356 (11)
C1—H1A0.9600C16—H160.9300
C1—H1B0.9600C17—H170.9300
C1—H1C0.9600C18—H18A0.9600
C2—C31.456 (10)C18—H18B0.9600
C3—C81.401 (11)C18—H18C0.9600
C3—C41.423 (10)C19—C201.506 (12)
C4—C51.408 (10)C19—H19A0.9700
C5—C61.366 (11)C19—H19B0.9700
C5—H50.9300C20—H20A0.9700
C6—C71.384 (11)C20—H20B0.9700
C7—C81.363 (11)
O3—Zn1—O188.4 (2)H9A—C9—H9C109.5
O3—Zn1—Cl2115.46 (18)H9B—C9—H9C109.5
O1—Zn1—Cl2116.08 (19)C11—C10—H10A109.5
O3—Zn1—Cl1108.8 (2)C11—C10—H10B109.5
O1—Zn1—Cl1108.74 (19)H10A—C10—H10B109.5
Cl2—Zn1—Cl1116.02 (10)C11—C10—H10C109.5
C4—O1—Zn1130.8 (5)H10A—C10—H10C109.5
C4—O1—H1109.5H10B—C10—H10C109.5
Zn1—O1—H1114.0N2—C11—C12118.4 (7)
C6—O2—C9117.5 (6)N2—C11—C10119.1 (7)
C13—O3—Zn1138.9 (5)C12—C11—C10122.5 (7)
C13—O3—H3109.5C13—C12—C17118.3 (7)
Zn1—O3—H3111.6C13—C12—C11122.5 (6)
C15—O4—C18118.4 (6)C17—C12—C11119.2 (7)
C2—N1—C19126.5 (6)O3—C13—C14120.9 (7)
C11—N2—C20129.3 (7)O3—C13—C12119.9 (7)
C2—C1—H1A109.5C14—C13—C12119.1 (7)
C2—C1—H1B109.5C15—C14—C13120.8 (7)
H1A—C1—H1B109.5C15—C14—H14119.6
C2—C1—H1C109.5C13—C14—H14119.6
H1A—C1—H1C109.5C14—C15—O4123.8 (7)
H1B—C1—H1C109.5C14—C15—C16122.2 (7)
N1—C2—C3119.1 (7)O4—C15—C16114.0 (7)
N1—C2—C1117.7 (7)C17—C16—C15118.4 (7)
C3—C2—C1123.2 (7)C17—C16—H16120.8
C8—C3—C4117.9 (7)C15—C16—H16120.8
C8—C3—C2119.8 (7)C16—C17—C12121.2 (7)
C4—C3—C2122.3 (7)C16—C17—H17119.4
O1—C4—C5119.2 (7)C12—C17—H17119.4
O1—C4—C3121.2 (7)O4—C18—H18A109.5
C5—C4—C3119.5 (7)O4—C18—H18B109.5
C6—C5—C4119.5 (8)H18A—C18—H18B109.5
C6—C5—H5120.3O4—C18—H18C109.5
C4—C5—H5120.3H18A—C18—H18C109.5
O2—C6—C5123.5 (8)H18B—C18—H18C109.5
O2—C6—C7114.8 (7)N1—C19—C20110.7 (7)
C5—C6—C7121.7 (8)N1—C19—H19A109.5
C8—C7—C6119.5 (8)C20—C19—H19A109.5
C8—C7—H7120.2N1—C19—H19B109.5
C6—C7—H7120.2C20—C19—H19B109.5
C7—C8—C3121.8 (8)H19A—C19—H19B108.1
C7—C8—H8119.1N2—C20—C19112.3 (7)
C3—C8—H8119.1N2—C20—H20A109.2
O2—C9—H9A109.5C19—C20—H20A109.2
O2—C9—H9B109.5N2—C20—H20B109.2
H9A—C9—H9B109.5C19—C20—H20B109.2
O2—C9—H9C109.5H20A—C20—H20B107.9
O3—Zn1—O1—C4168.6 (7)C2—C3—C8—C7177.8 (8)
Cl2—Zn1—O1—C473.7 (7)C20—N2—C11—C12178.7 (8)
Cl1—Zn1—O1—C459.3 (7)C20—N2—C11—C101.5 (14)
O1—Zn1—O3—C13147.7 (8)N2—C11—C12—C131.4 (12)
Cl2—Zn1—O3—C1329.4 (9)C10—C11—C12—C13178.4 (8)
Cl1—Zn1—O3—C13103.0 (8)N2—C11—C12—C17176.0 (8)
C19—N1—C2—C3179.0 (8)C10—C11—C12—C174.2 (12)
C19—N1—C2—C10.5 (13)Zn1—O3—C13—C141.4 (13)
N1—C2—C3—C8177.0 (8)Zn1—O3—C13—C12179.0 (6)
C1—C2—C3—C82.5 (12)C17—C12—C13—O3179.5 (7)
N1—C2—C3—C40.7 (12)C11—C12—C13—O32.2 (12)
C1—C2—C3—C4179.8 (8)C17—C12—C13—C142.8 (11)
Zn1—O1—C4—C528.7 (11)C11—C12—C13—C14179.8 (8)
Zn1—O1—C4—C3153.5 (6)O3—C13—C14—C15178.9 (7)
C8—C3—C4—O1179.0 (8)C12—C13—C14—C153.5 (12)
C2—C3—C4—O11.3 (12)C13—C14—C15—O4177.3 (7)
C8—C3—C4—C53.2 (12)C13—C14—C15—C162.6 (13)
C2—C3—C4—C5179.0 (8)C18—O4—C15—C142.4 (12)
O1—C4—C5—C6178.2 (7)C18—O4—C15—C16177.5 (8)
C3—C4—C5—C64.0 (12)C14—C15—C16—C171.0 (13)
C9—O2—C6—C55.6 (13)O4—C15—C16—C17178.9 (8)
C9—O2—C6—C7171.7 (8)C15—C16—C17—C120.4 (13)
C4—C5—C6—O2178.5 (8)C13—C12—C17—C161.3 (12)
C4—C5—C6—C71.5 (13)C11—C12—C17—C16178.8 (8)
O2—C6—C7—C8175.5 (8)C2—N1—C19—C20138.3 (8)
C5—C6—C7—C81.8 (14)C11—N2—C20—C19114.8 (10)
C6—C7—C8—C32.6 (14)N1—C19—C20—N260.1 (10)
C4—C3—C8—C70.0 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.852.582 (8)149
O3—H3···N20.821.782.529 (8)150
 

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