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The title complex, [ZnCl2(C19H22N2O4)], is a mononuclear compound; the central zinc ion is coordinated by two Cl ligands and two N atoms of the bis­(3,4-methyl­enedioxy­benz­yl)­propane-1,3-diamine in a distorted tetra­hedral geometry. The complex adopts a `hawk' conformation. The mol­ecules are linked by pairs of N—H...Cl hydrogen bonds into a C22(8)C22(8)[R22(8)R22(8)] chain of rings along the [001] direction and the mol­ecules are linked by a pair of C—H...O and also by a pair of C—H...Cl hydrogen bonds into a chain of alternating R22(6) rings and R22(20) rings along the [111] direction. The combination of the [111] chain and the [001] chain generates [1\overline{1}0] stacks.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806036798/at2104sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806036798/at2104Isup2.hkl
Contains datablock I

CCDC reference: 616609

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.030
  • wR factor = 0.080
  • Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Zn1 - Cl2 .. 5.44 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O4 PLAT480_ALERT_4_C Long H...A H-Bond Reported H11A .. O1 .. 2.72 Ang.
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 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Bis[N,N'-bis(3,4-methylenedioxybenzyl)propane-1,3-diamine]dichlorozinc(II) top
Crystal data top
[ZnCl2(C19H22N2O4)]F(000) = 984
Mr = 478.66Dx = 1.531 Mg m3
Monoclinic, P21/cMelting point: 493 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 15.612 (4) ÅCell parameters from 3623 reflections
b = 12.934 (3) Åθ = 2.6–25.4°
c = 10.318 (3) ŵ = 1.47 mm1
β = 94.557 (3)°T = 298 K
V = 2076.9 (9) Å3Block, colourless
Z = 40.42 × 0.22 × 0.15 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3650 independent reflections
Radiation source: fine-focus sealed tube2705 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
φ and ω scansθmax = 25.0°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1718
Tmin = 0.578, Tmax = 0.810k = 1315
10572 measured reflectionsl = 1212
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)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0318P)2 + 0.8P]
where P = (Fo2 + 2Fc2)/3
3650 reflections(Δ/σ)max < 0.001
253 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.21 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
Zn10.71993 (2)0.31447 (3)0.35088 (3)0.03686 (12)
Cl10.80701 (5)0.18928 (6)0.30126 (8)0.0523 (2)
Cl20.67054 (5)0.40192 (6)0.17281 (8)0.0549 (2)
N10.76923 (13)0.41748 (18)0.4874 (2)0.0383 (6)
H10.78420.38150.56160.046*
N20.61120 (14)0.27548 (18)0.4416 (2)0.0390 (6)
H20.62780.23990.51540.047*
O11.03020 (17)0.5245 (2)0.8567 (2)0.0802 (8)
O21.01308 (17)0.7023 (2)0.8513 (3)0.0778 (8)
O30.33469 (14)0.05721 (17)0.6252 (2)0.0581 (6)
O40.22258 (14)0.1311 (2)0.5005 (3)0.0766 (8)
C10.70058 (18)0.4914 (2)0.5161 (3)0.0480 (8)
H1A0.68050.52720.43680.058*
H1B0.72410.54260.57780.058*
C20.62548 (18)0.4377 (2)0.5715 (3)0.0481 (8)
H2A0.64790.39400.64270.058*
H2B0.59000.49010.60800.058*
C30.56836 (17)0.3721 (2)0.4790 (3)0.0452 (7)
H3A0.51640.35460.51990.054*
H3B0.55190.41190.40140.054*
C40.84834 (19)0.4699 (3)0.4470 (3)0.0521 (8)
H4A0.83290.51230.37120.062*
H4B0.88850.41770.42210.062*
C50.89242 (18)0.5370 (2)0.5519 (3)0.0432 (7)
C60.94134 (18)0.4897 (2)0.6544 (3)0.0456 (8)
H60.94800.41830.65860.055*
C70.97896 (18)0.5531 (3)0.7480 (3)0.0492 (8)
C80.9699 (2)0.6584 (3)0.7440 (3)0.0530 (9)
C90.9236 (2)0.7064 (3)0.6454 (4)0.0623 (10)
H90.91790.77790.64260.075*
C100.8847 (2)0.6435 (3)0.5482 (4)0.0583 (9)
H100.85260.67400.47860.070*
C111.0598 (3)0.6194 (4)0.9135 (4)0.0920 (15)
H11A1.05150.61941.00570.110*
H11B1.12060.62770.90340.110*
C120.55559 (18)0.2068 (2)0.3555 (3)0.0475 (8)
H12A0.58380.14020.35150.057*
H12B0.55190.23570.26850.057*
C130.46524 (18)0.1887 (2)0.3935 (3)0.0406 (7)
C140.44958 (18)0.1283 (2)0.5014 (3)0.0406 (7)
H140.49430.09910.55400.049*
C150.36593 (19)0.1138 (2)0.5261 (3)0.0409 (7)
C160.2993 (2)0.1570 (2)0.4516 (4)0.0526 (9)
C170.3121 (2)0.2167 (3)0.3474 (4)0.0736 (12)
H170.26660.24640.29690.088*
C180.3974 (2)0.2315 (3)0.3194 (4)0.0659 (10)
H180.40860.27190.24800.079*
C190.2434 (2)0.0562 (3)0.5951 (4)0.0677 (10)
H19A0.22520.01150.56300.081*
H19B0.21430.07100.67260.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.03606 (19)0.0413 (2)0.03308 (19)0.00045 (15)0.00213 (13)0.00102 (16)
Cl10.0505 (4)0.0527 (5)0.0543 (5)0.0131 (4)0.0073 (4)0.0017 (4)
Cl20.0688 (5)0.0530 (5)0.0408 (5)0.0033 (4)0.0092 (4)0.0104 (4)
N10.0345 (12)0.0441 (14)0.0365 (14)0.0034 (11)0.0032 (10)0.0036 (11)
N20.0384 (13)0.0437 (14)0.0350 (14)0.0015 (11)0.0037 (11)0.0008 (11)
O10.0832 (18)0.088 (2)0.0641 (17)0.0190 (15)0.0244 (15)0.0087 (15)
O20.0756 (18)0.084 (2)0.0733 (19)0.0230 (15)0.0001 (15)0.0262 (16)
O30.0584 (14)0.0653 (15)0.0510 (14)0.0116 (11)0.0075 (11)0.0161 (12)
O40.0423 (13)0.0753 (18)0.114 (2)0.0004 (12)0.0165 (14)0.0343 (17)
C10.0471 (17)0.0465 (19)0.051 (2)0.0028 (15)0.0038 (15)0.0095 (16)
C20.0408 (17)0.056 (2)0.049 (2)0.0038 (15)0.0094 (15)0.0089 (16)
C30.0357 (16)0.0474 (19)0.053 (2)0.0026 (14)0.0071 (14)0.0030 (16)
C40.0455 (18)0.064 (2)0.048 (2)0.0113 (16)0.0118 (15)0.0037 (17)
C50.0360 (16)0.051 (2)0.0435 (18)0.0090 (14)0.0099 (14)0.0046 (15)
C60.0422 (17)0.0413 (18)0.054 (2)0.0051 (14)0.0105 (15)0.0012 (16)
C70.0396 (18)0.063 (2)0.0450 (19)0.0109 (16)0.0053 (15)0.0029 (17)
C80.0444 (19)0.058 (2)0.058 (2)0.0162 (16)0.0117 (17)0.0166 (18)
C90.058 (2)0.045 (2)0.084 (3)0.0051 (17)0.004 (2)0.0074 (19)
C100.0505 (19)0.055 (2)0.068 (2)0.0035 (17)0.0045 (17)0.0044 (19)
C110.097 (3)0.117 (4)0.059 (3)0.044 (3)0.014 (2)0.006 (3)
C120.0496 (18)0.050 (2)0.0443 (18)0.0072 (15)0.0094 (15)0.0050 (15)
C130.0422 (16)0.0370 (16)0.0426 (17)0.0045 (14)0.0042 (13)0.0005 (14)
C140.0419 (16)0.0404 (17)0.0383 (17)0.0032 (14)0.0034 (13)0.0028 (14)
C150.0505 (18)0.0346 (16)0.0375 (17)0.0076 (14)0.0031 (14)0.0039 (14)
C160.0422 (18)0.0467 (19)0.069 (2)0.0016 (15)0.0057 (17)0.0098 (17)
C170.044 (2)0.083 (3)0.092 (3)0.0061 (18)0.0045 (19)0.044 (2)
C180.057 (2)0.077 (3)0.063 (2)0.0084 (19)0.0038 (18)0.034 (2)
C190.060 (2)0.064 (2)0.080 (3)0.0122 (19)0.016 (2)0.011 (2)
Geometric parameters (Å, º) top
Zn1—N12.045 (2)C4—H4A0.9700
Zn1—N22.065 (2)C4—H4B0.9700
Zn1—Cl12.2007 (9)C5—C101.383 (4)
Zn1—Cl22.2416 (9)C5—C61.395 (4)
N1—C11.484 (4)C6—C71.364 (4)
N1—C41.497 (3)C6—H60.9300
N1—H10.9100C7—C81.369 (4)
N2—C31.483 (4)C8—C91.351 (5)
N2—C121.487 (4)C9—C101.392 (5)
N2—H20.9100C9—H90.9300
O1—C71.376 (4)C10—H100.9300
O1—C111.421 (5)C11—H11A0.9700
O2—C81.373 (4)C11—H11B0.9700
O2—C111.421 (5)C12—C131.512 (4)
O3—C151.377 (3)C12—H12A0.9700
O3—C191.434 (4)C12—H12B0.9700
O4—C161.377 (4)C13—C181.372 (4)
O4—C191.395 (4)C13—C141.398 (4)
C1—C21.514 (4)C14—C151.363 (4)
C1—H1A0.9700C14—H140.9300
C1—H1B0.9700C15—C161.364 (4)
C2—C31.514 (4)C16—C171.352 (5)
C2—H2A0.9700C17—C181.398 (4)
C2—H2B0.9700C17—H170.9300
C3—H3A0.9700C18—H180.9300
C3—H3B0.9700C19—H19A0.9700
C4—C51.510 (4)C19—H19B0.9700
N1—Zn1—N297.17 (9)C7—C6—H6121.6
N1—Zn1—Cl1115.73 (7)C5—C6—H6121.6
N2—Zn1—Cl1118.10 (7)C6—C7—C8122.6 (3)
N1—Zn1—Cl2108.80 (7)C6—C7—O1127.3 (3)
N2—Zn1—Cl2104.66 (7)C8—C7—O1110.1 (3)
Cl1—Zn1—Cl2111.05 (4)C9—C8—C7121.9 (3)
C1—N1—C4112.9 (2)C9—C8—O2128.0 (3)
C1—N1—Zn1108.61 (17)C7—C8—O2110.1 (3)
C4—N1—Zn1112.14 (17)C8—C9—C10116.8 (3)
C1—N1—H1107.7C8—C9—H9121.6
C4—N1—H1107.7C10—C9—H9121.6
Zn1—N1—H1107.7C5—C10—C9122.0 (3)
C3—N2—C12113.9 (2)C5—C10—H10119.0
C3—N2—Zn1108.44 (17)C9—C10—H10119.0
C12—N2—Zn1109.72 (17)O2—C11—O1109.1 (3)
C3—N2—H2108.2O2—C11—H11A109.9
C12—N2—H2108.2O1—C11—H11A109.9
Zn1—N2—H2108.2O2—C11—H11B109.9
C7—O1—C11104.6 (3)O1—C11—H11B109.9
C8—O2—C11104.7 (3)H11A—C11—H11B108.3
C15—O3—C19104.4 (2)N2—C12—C13116.7 (2)
C16—O4—C19105.3 (2)N2—C12—H12A108.1
N1—C1—C2111.9 (2)C13—C12—H12A108.1
N1—C1—H1A109.2N2—C12—H12B108.1
C2—C1—H1A109.2C13—C12—H12B108.1
N1—C1—H1B109.2H12A—C12—H12B107.3
C2—C1—H1B109.2C18—C13—C14119.6 (3)
H1A—C1—H1B107.9C18—C13—C12119.2 (3)
C3—C2—C1117.0 (3)C14—C13—C12121.2 (3)
C3—C2—H2A108.0C15—C14—C13117.2 (3)
C1—C2—H2A108.0C15—C14—H14121.4
C3—C2—H2B108.0C13—C14—H14121.4
C1—C2—H2B108.0C14—C15—C16122.5 (3)
H2A—C2—H2B107.3C14—C15—O3127.8 (3)
N2—C3—C2112.4 (2)C16—C15—O3109.7 (3)
N2—C3—H3A109.1C17—C16—C15121.8 (3)
C2—C3—H3A109.1C17—C16—O4128.3 (3)
N2—C3—H3B109.1C15—C16—O4109.9 (3)
C2—C3—H3B109.1C16—C17—C18116.5 (3)
H3A—C3—H3B107.9C16—C17—H17121.7
N1—C4—C5113.6 (2)C18—C17—H17121.7
N1—C4—H4A108.9C13—C18—C17122.3 (3)
C5—C4—H4A108.9C13—C18—H18118.8
N1—C4—H4B108.9C17—C18—H18118.8
C5—C4—H4B108.9O4—C19—O3108.5 (3)
H4A—C4—H4B107.7O4—C19—H19A110.0
C10—C5—C6119.9 (3)O3—C19—H19A110.0
C10—C5—C4121.3 (3)O4—C19—H19B110.0
C6—C5—C4118.8 (3)O3—C19—H19B110.0
C7—C6—C5116.9 (3)H19A—C19—H19B108.4
N2—Zn1—N1—C149.91 (19)C11—O2—C8—C9172.4 (4)
Cl1—Zn1—N1—C1175.90 (16)C11—O2—C8—C78.0 (4)
Cl2—Zn1—N1—C158.28 (19)C7—C8—C9—C100.5 (5)
N2—Zn1—N1—C4175.33 (19)O2—C8—C9—C10179.1 (3)
Cl1—Zn1—N1—C458.7 (2)C6—C5—C10—C91.0 (5)
Cl2—Zn1—N1—C467.1 (2)C4—C5—C10—C9178.7 (3)
N1—Zn1—N2—C349.18 (19)C8—C9—C10—C50.4 (5)
Cl1—Zn1—N2—C3173.45 (15)C8—O2—C11—O111.5 (4)
Cl2—Zn1—N2—C362.45 (18)C7—O1—C11—O210.7 (4)
N1—Zn1—N2—C12174.18 (19)C3—N2—C12—C1345.8 (4)
Cl1—Zn1—N2—C1261.55 (19)Zn1—N2—C12—C13167.5 (2)
Cl2—Zn1—N2—C1262.55 (19)N2—C12—C13—C18109.5 (4)
C4—N1—C1—C2173.4 (2)N2—C12—C13—C1471.4 (4)
Zn1—N1—C1—C261.6 (3)C18—C13—C14—C151.0 (5)
N1—C1—C2—C371.8 (3)C12—C13—C14—C15178.1 (3)
C12—N2—C3—C2177.3 (2)C13—C14—C15—C161.1 (5)
Zn1—N2—C3—C260.2 (3)C13—C14—C15—O3179.5 (3)
C1—C2—C3—N271.3 (4)C19—O3—C15—C14172.3 (3)
C1—N1—C4—C563.8 (3)C19—O3—C15—C168.2 (3)
Zn1—N1—C4—C5173.2 (2)C14—C15—C16—C170.5 (5)
N1—C4—C5—C10103.2 (3)O3—C15—C16—C17180.0 (3)
N1—C4—C5—C676.5 (3)C14—C15—C16—O4178.8 (3)
C10—C5—C6—C70.7 (4)O3—C15—C16—O40.7 (4)
C4—C5—C6—C7179.0 (3)C19—O4—C16—C17171.2 (4)
C5—C6—C7—C80.2 (5)C19—O4—C16—C159.6 (4)
C5—C6—C7—O1179.5 (3)C15—C16—C17—C180.3 (6)
C11—O1—C7—C6173.9 (3)O4—C16—C17—C18179.4 (4)
C11—O1—C7—C85.7 (4)C14—C13—C18—C170.2 (6)
C6—C7—C8—C90.8 (5)C12—C13—C18—C17178.9 (4)
O1—C7—C8—C9178.9 (3)C16—C17—C18—C130.4 (6)
C6—C7—C8—O2178.9 (3)C16—O4—C19—O314.7 (4)
O1—C7—C8—O21.4 (4)C15—O3—C19—O414.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Cl1i0.912.633.526 (3)167
N2—H2···Cl2i0.912.513.386 (3)163
C11—H11A···O1ii0.972.723.404 (5)128
C19—H19A···Cl1iii0.972.763.461 (4)130
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+2, y+1, z+2; (iii) x+1, y, z+1.
 

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