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In the title compound, [ZnCl2(C12H17N3O3)], a mononuclear Schiff base zinc(II) complex, the Zn atom is tetra­hedrally coordinated by one imine N atom and one phenolate O-atom of the Schiff base ligand and by two terminal chloride anions. In the crystal structure, symmetry-related mol­ecules are linked through inter­molecular N—H...Cl, N—H...O and C—H...Cl hydrogen bonds, forming chains running parallel to the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807006010/su2002sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807006010/su2002Isup2.hkl
Contains datablock I

CCDC reference: 640499

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.033
  • wR factor = 0.084
  • Data-to-parameter ratio = 18.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.97 PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - C7 .. 5.02 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Zn1 - Cl1 .. 5.51 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Zn1 - Cl2 .. 5.89 su PLAT432_ALERT_2_C Short Inter X...Y Contact Cl2 .. C7 .. 3.24 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 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 4 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 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, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL.

Dichloro{4-nitro-2-[(2-isopropylaminoethylimino)methyl]phenolato}zinc(II) top
Crystal data top
[ZnCl2(C12H17N3O3)]F(000) = 792
Mr = 387.56Dx = 1.612 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4303 reflections
a = 11.721 (1) Åθ = 2.4–26.0°
b = 11.675 (1) ŵ = 1.88 mm1
c = 12.356 (2) ÅT = 298 K
β = 109.191 (1)°Block, yellow
V = 1596.9 (3) Å30.33 × 0.29 × 0.23 mm
Z = 4
Data collection top
Bruker SMART APEX area-detector
diffractometer
3631 independent reflections
Radiation source: fine-focus sealed tube2929 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1515
Tmin = 0.575, Tmax = 0.671k = 1514
13138 measured reflectionsl = 1615
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0416P)2 + 0.2873P]
where P = (Fo2 + 2Fc2)/3
3631 reflections(Δ/σ)max < 0.001
192 parametersΔρmax = 0.45 e Å3
0 restraintsΔρmin = 0.24 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
Zn11.02182 (2)0.92077 (2)0.25907 (2)0.03657 (10)
Cl10.84538 (6)0.90705 (5)0.29134 (6)0.04670 (16)
Cl21.04556 (6)1.06472 (5)0.15077 (5)0.04535 (16)
O11.15549 (15)0.92308 (12)0.40435 (13)0.0404 (4)
O21.4097 (2)0.45170 (18)0.55851 (19)0.0771 (7)
O31.5038 (2)0.5559 (2)0.7026 (2)0.0854 (7)
N11.06479 (15)0.77315 (14)0.20042 (14)0.0314 (4)
N20.81169 (16)0.67098 (15)0.09987 (16)0.0371 (4)
H2A0.85110.67390.17580.044*
H2B0.82110.59980.07610.044*
N31.4287 (2)0.5435 (2)0.6085 (2)0.0561 (6)
C11.21822 (19)0.72986 (17)0.38531 (18)0.0326 (5)
C21.21922 (19)0.83231 (17)0.44774 (18)0.0334 (5)
C31.2937 (2)0.83498 (19)0.56417 (19)0.0388 (5)
H31.29710.90170.60630.047*
C41.3604 (2)0.7426 (2)0.6164 (2)0.0445 (6)
H41.40770.74620.69320.053*
C51.3572 (2)0.6429 (2)0.5536 (2)0.0423 (5)
C61.2885 (2)0.6363 (2)0.4406 (2)0.0394 (5)
H61.28820.56920.40000.047*
C71.14665 (19)0.70878 (18)0.26600 (18)0.0329 (5)
H71.16230.64090.23410.039*
C81.0059 (2)0.73661 (19)0.08119 (17)0.0357 (5)
H8A1.02370.65640.07390.043*
H8B1.03870.78030.03150.043*
C90.8705 (2)0.75286 (18)0.04259 (18)0.0363 (5)
H9A0.85250.83060.05970.044*
H9B0.83750.74220.03970.044*
C100.6784 (2)0.6902 (2)0.0798 (2)0.0467 (6)
H100.66610.76970.09870.056*
C110.6421 (3)0.6115 (3)0.1599 (3)0.0766 (10)
H11A0.65770.53350.14430.115*
H11B0.55760.62090.14850.115*
H11C0.68810.63010.23770.115*
C120.6064 (3)0.6685 (3)0.0440 (3)0.0670 (8)
H12A0.63500.71760.09190.100*
H12B0.52260.68420.05650.100*
H12C0.61560.58990.06260.100*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.04232 (17)0.02788 (15)0.03721 (16)0.00039 (10)0.00994 (12)0.00268 (10)
Cl10.0501 (4)0.0403 (3)0.0546 (4)0.0020 (3)0.0239 (3)0.0060 (3)
Cl20.0609 (4)0.0373 (3)0.0383 (3)0.0003 (3)0.0170 (3)0.0042 (2)
O10.0462 (10)0.0313 (8)0.0386 (9)0.0002 (7)0.0068 (7)0.0054 (6)
O20.0914 (17)0.0473 (12)0.0731 (15)0.0155 (11)0.0006 (12)0.0077 (11)
O30.0891 (17)0.0796 (15)0.0575 (13)0.0162 (13)0.0167 (12)0.0106 (11)
N10.0362 (10)0.0272 (9)0.0301 (9)0.0017 (7)0.0100 (8)0.0008 (7)
N20.0358 (10)0.0355 (10)0.0356 (10)0.0025 (8)0.0058 (8)0.0001 (8)
N30.0549 (14)0.0527 (14)0.0512 (14)0.0048 (11)0.0047 (11)0.0141 (11)
C10.0323 (11)0.0306 (11)0.0339 (11)0.0032 (9)0.0095 (9)0.0002 (9)
C20.0324 (11)0.0332 (11)0.0360 (11)0.0065 (9)0.0133 (9)0.0004 (9)
C30.0393 (13)0.0416 (13)0.0345 (12)0.0079 (10)0.0108 (10)0.0057 (10)
C40.0395 (13)0.0555 (15)0.0337 (12)0.0096 (11)0.0056 (10)0.0030 (11)
C50.0383 (13)0.0414 (13)0.0431 (13)0.0020 (10)0.0077 (10)0.0079 (11)
C60.0400 (13)0.0340 (12)0.0422 (13)0.0023 (10)0.0106 (10)0.0009 (10)
C70.0385 (12)0.0282 (10)0.0345 (11)0.0041 (9)0.0153 (9)0.0030 (9)
C80.0441 (13)0.0353 (12)0.0288 (11)0.0004 (9)0.0135 (10)0.0012 (9)
C90.0455 (13)0.0327 (11)0.0271 (11)0.0029 (9)0.0072 (9)0.0001 (9)
C100.0353 (13)0.0456 (14)0.0556 (15)0.0067 (10)0.0097 (11)0.0039 (12)
C110.0423 (16)0.094 (2)0.101 (3)0.0079 (16)0.0333 (17)0.021 (2)
C120.0423 (15)0.075 (2)0.0678 (19)0.0019 (14)0.0035 (14)0.0131 (16)
Geometric parameters (Å, º) top
Zn1—O11.957 (2)C4—C51.392 (4)
Zn1—N11.997 (2)C4—H40.9300
Zn1—Cl22.222 (1)C5—C61.365 (3)
Zn1—Cl12.237 (1)C6—H60.9300
O1—C21.306 (2)C7—H70.9300
O2—N31.220 (3)C8—C91.511 (3)
O3—N31.214 (3)C8—H8A0.9700
N1—C71.277 (3)C8—H8B0.9700
N1—C81.470 (3)C9—H9A0.9700
N2—C91.487 (3)C9—H9B0.9700
N2—C101.516 (3)C10—C121.506 (4)
N2—H2A0.9000C10—C111.510 (4)
N2—H2B0.9000C10—H100.9800
N3—C51.462 (3)C11—H11A0.9600
C1—C61.403 (3)C11—H11B0.9600
C1—C21.421 (3)C11—H11C0.9600
C1—C71.458 (3)C12—H12A0.9600
C2—C31.417 (3)C12—H12B0.9600
C3—C41.364 (3)C12—H12C0.9600
C3—H30.9300
O1—Zn1—N197.09 (7)C5—C6—H6119.7
O1—Zn1—Cl2108.72 (6)C1—C6—H6119.7
N1—Zn1—Cl2109.73 (6)N1—C7—C1127.2 (2)
O1—Zn1—Cl1110.24 (6)N1—C7—H7116.4
N1—Zn1—Cl1111.17 (5)C1—C7—H7116.4
Cl2—Zn1—Cl1117.88 (3)N1—C8—C9112.25 (17)
C2—O1—Zn1122.88 (13)N1—C8—H8A109.2
C7—N1—C8118.21 (18)C9—C8—H8A109.2
C7—N1—Zn1120.27 (14)N1—C8—H8B109.2
C8—N1—Zn1121.51 (13)C9—C8—H8B109.2
C9—N2—C10116.16 (18)H8A—C8—H8B107.9
C9—N2—H2A108.2N2—C9—C8111.83 (17)
C10—N2—H2A108.2N2—C9—H9A109.3
C9—N2—H2B108.2C8—C9—H9A109.3
C10—N2—H2B108.2N2—C9—H9B109.3
H2A—N2—H2B107.4C8—C9—H9B109.3
O3—N3—O2123.0 (2)H9A—C9—H9B107.9
O3—N3—C5118.3 (2)C12—C10—C11112.3 (3)
O2—N3—C5118.7 (2)C12—C10—N2110.2 (2)
C6—C1—C2119.5 (2)C11—C10—N2107.4 (2)
C6—C1—C7114.31 (19)C12—C10—H10109.0
C2—C1—C7126.19 (19)C11—C10—H10109.0
O1—C2—C3118.52 (19)N2—C10—H10109.0
O1—C2—C1123.96 (19)C10—C11—H11A109.5
C3—C2—C1117.52 (19)C10—C11—H11B109.5
C4—C3—C2121.9 (2)H11A—C11—H11B109.5
C4—C3—H3119.0C10—C11—H11C109.5
C2—C3—H3119.0H11A—C11—H11C109.5
C3—C4—C5119.4 (2)H11B—C11—H11C109.5
C3—C4—H4120.3C10—C12—H12A109.5
C5—C4—H4120.3C10—C12—H12B109.5
C6—C5—C4121.0 (2)H12A—C12—H12B109.5
C6—C5—N3119.0 (2)C10—C12—H12C109.5
C4—C5—N3119.9 (2)H12A—C12—H12C109.5
C5—C6—C1120.6 (2)H12B—C12—H12C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···Cl2i0.902.443.231 (2)146
N2—H2B···O1i0.902.082.922 (3)154
C7—H7···Cl1i0.932.753.600 (3)153
C8—H8B···Cl2ii0.972.803.581 (3)138
C9—H9B···Cl1iii0.972.743.551 (3)141
Symmetry codes: (i) x+2, y1/2, z+1/2; (ii) x+2, y+2, z; (iii) x, y+3/2, z1/2.
 

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