{Bis[2-(3,4-methyl­enedioxy­benzyl­amino)eth­yl]amine}dichloridozinc(II) hemihydrate

Han, L.-J.; Yang, S.-P.; Wang, D.-Q.; Xia, H.-T.

doi:10.1107/S1600536807054931

Buy article online - an online subscription or single-article purchase is required to access this article.

{Bis[2-(3,4-methylenedioxybenzylamino)ethyl]amine}dichloridozinc(II) hemihydrate

L.-J. Han, S.-P. Yang, D.-Q. Wang and H.-T. Xia

In the title compound, [ZnCl₂(C₂₀H₂₅N₃O₄)]·0.5H₂O, the Zn^II ion assumes a trigonal bipyramidal coordination geometry formed by a tridentate amine ligand and two Cl^- anions. The tridentate amine ligand chelates the Zn^II ion in a meridional configuration. The extensive hydrogen-bonding network helps to stabilize the crystal structure.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807054931/xu2337sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807054931/xu2337Isup2.hkl Contains datablock I

CCDC reference: 656515

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.017 Å
Disorder in solvent or counterion
R factor = 0.104
wR factor = 0.277
Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT341_ALERT_3_B Low Bond Precision on C-C Bonds (x 1000) Ang ...         17

Alert level C
RFACG01_ALERT_3_C  The value of the R factor is > 0.10
            R factor given   0.104
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.277
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT084_ALERT_2_C High R2 Value ..................................       0.28
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.51
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O3
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.
PLAT417_ALERT_2_C Short Inter D-H..H-D       H2     ..  H5A     ..       2.11 Ang.

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of N1     = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of N2     = ...          R

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  10 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   5 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
   3 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

Comment top

We have reported recently the crystyl structure of a Zn^II complex (Han et al., 2006). As part of our study of the Zn^II complexes with the diamine derives, we report here the crystal structure of a new Zn^II complex.

The title complex is a mononuclear compound, and the central zinc ion is five-coordinated by two Cl^- ions and three N atoms from a tridentate ligand N,N'-bis[(3,4-methylenedioxybenzyl)-2,2'-diaminodiethyl]amine (Fig. 1). The tridentate ligand chelates to the Zn^II ion in a meridional configuration. The coordination geometry around the Zn^II ion is a distorted trigonal bipyramid. The Zn—Cl and Zn—N bond lengths (Table 1) are slightly longer than those found in the related Zn^II complex (Han et al., 2006).

The extensive hydrogen bonding network helps to stabilize the crystal structure (Table. 2).

Related literature top

For related literature, see: Han et al. (2006).

Experimental top

The ethanol solution (20 ml) of N,N'-bis[(3,4-methylenedioxybenzyl)-2,2'-diaminodiethyl]amine (1.86 g, 5 mmol) was mixed with the ethanol solution (30 ml) of zinc chloride (1.36 g, 10 mmol), the mixture was stirred for 4 h at 340 K. The crude solid obtained was filtered off and washed successively with ethanol. Single crystals of the title compound were obtained by slow evaporation of a DMF-chloroform-ethanol (1:5:10) solution of the crude product over a period of three weeks.

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: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL.

Figures top

Fig. 1. The molecule of the title compound. Displacement ellipsoids are drawn at the 30% probability level.

{Bis[2-(3,4-methylenedioxybenzylamino)ethyl]amine}dichloridozinc(II) hemihydrate top

Crystal data top

[ZnCl₂(C₂₀H₂₅N₃O₄)]·0.5H₂O	F(000) = 1068
M_r = 516.71	D_x = 1.514 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 504–506 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 24.042 (3) Å	Cell parameters from 2613 reflections
b = 13.0193 (18) Å	θ = 3.0–22.0°
c = 7.2678 (14) Å	µ = 1.35 mm⁻¹
β = 94.934 (2)°	T = 298 K
V = 2266.5 (6) Å³	Prism, colorless
Z = 4	0.57 × 0.15 × 0.12 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4003 independent reflections
Radiation source: fine-focus sealed tube	2735 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.077
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −27→28
T_min = 0.513, T_max = 0.855	k = −11→15
11175 measured reflections	l = −8→8

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.104	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.277	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0881P)² + 21.9915P] where P = (F_o² + 2F_c²)/3
4003 reflections	(Δ/σ)_max < 0.001
280 parameters	Δρ_max = 1.46 e Å⁻³
0 restraints	Δρ_min = −0.58 e Å⁻³

Crystal data top

[ZnCl₂(C₂₀H₂₅N₃O₄)]·0.5H₂O	V = 2266.5 (6) Å³
M_r = 516.71	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 24.042 (3) Å	µ = 1.35 mm⁻¹
b = 13.0193 (18) Å	T = 298 K
c = 7.2678 (14) Å	0.57 × 0.15 × 0.12 mm
β = 94.934 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4003 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2735 reflections with I > 2σ(I)
T_min = 0.513, T_max = 0.855	R_int = 0.077
11175 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.104	0 restraints
wR(F²) = 0.277	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0881P)² + 21.9915P] where P = (F_o² + 2F_c²)/3
4003 reflections	Δρ_max = 1.46 e Å⁻³
280 parameters	Δρ_min = −0.58 e Å⁻³

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Zn1	0.25115 (5)	0.52956 (9)	0.26489 (17)	0.0442 (4)
Cl1	0.22268 (12)	0.6661 (2)	0.0855 (4)	0.0546 (7)
Cl2	0.28847 (14)	0.3967 (3)	0.0916 (6)	0.0838 (11)
N1	0.3374 (3)	0.5641 (7)	0.3637 (12)	0.049 (2)
H1	0.3545	0.5030	0.3920	0.058*
N2	0.1760 (4)	0.4473 (7)	0.3044 (12)	0.049 (2)
H2	0.1863	0.3821	0.3374	0.059*
N3	0.2405 (3)	0.5717 (7)	0.5416 (12)	0.048 (2)
H3	0.2278	0.6376	0.5380	0.058*
O1	0.5505 (3)	0.7611 (6)	0.4817 (13)	0.068 (2)
O2	0.6010 (3)	0.6208 (7)	0.4070 (13)	0.067 (2)
O3	−0.0658 (4)	0.3908 (7)	0.2274 (16)	0.086 (3)
O4	−0.0591 (3)	0.2137 (7)	0.2272 (13)	0.071 (2)
O5	0.2238 (8)	0.2319 (15)	0.295 (4)	0.118 (10)	0.50
H5A	0.2440	0.2756	0.2449	0.141*	0.50
H5B	0.2443	0.1989	0.3760	0.141*	0.50
C1	0.3688 (5)	0.6133 (10)	0.2204 (16)	0.062 (3)
H1A	0.3567	0.6842	0.2052	0.074*
H1B	0.3600	0.5784	0.1037	0.074*
C2	0.4317 (5)	0.6111 (10)	0.2678 (16)	0.057 (3)
C3	0.4591 (5)	0.6960 (8)	0.3597 (16)	0.055 (3)
H3A	0.4395	0.7541	0.3912	0.067*
C4	0.5154 (4)	0.6885 (8)	0.3996 (16)	0.050 (3)
C5	0.5446 (4)	0.6027 (9)	0.3560 (15)	0.050 (3)
C6	0.5194 (5)	0.5227 (9)	0.2668 (16)	0.055 (3)
H6	0.5397	0.4654	0.2358	0.066*
C7	0.4631 (5)	0.5277 (9)	0.2231 (17)	0.060 (3)
H7	0.4454	0.4728	0.1608	0.073*
C8	0.6019 (5)	0.7118 (11)	0.521 (2)	0.076 (4)
H8A	0.6071	0.6934	0.6504	0.091*
H8B	0.6322	0.7568	0.4925	0.091*
C9	0.1359 (5)	0.4388 (9)	0.1357 (16)	0.058 (3)
H9A	0.1554	0.4092	0.0369	0.070*
H9B	0.1242	0.5074	0.0975	0.070*
C10	0.0845 (5)	0.3750 (9)	0.1598 (16)	0.054 (3)
C11	0.0345 (5)	0.4233 (9)	0.1839 (17)	0.060 (3)
H11	0.0317	0.4945	0.1858	0.072*
C12	−0.0115 (4)	0.3608 (9)	0.2050 (16)	0.056 (3)
C13	−0.0067 (4)	0.2563 (9)	0.2025 (17)	0.055 (3)
C14	0.0417 (5)	0.2097 (9)	0.1823 (17)	0.057 (3)
H14	0.0441	0.1384	0.1812	0.068*
C15	0.0885 (5)	0.2694 (10)	0.1631 (17)	0.059 (3)
H15	0.1228	0.2380	0.1524	0.071*
C16	−0.0944 (5)	0.2985 (10)	0.252 (2)	0.069 (3)
H16A	−0.1270	0.2948	0.1642	0.083*
H16B	−0.1069	0.2966	0.3756	0.083*
C17	0.3368 (5)	0.6222 (10)	0.5386 (17)	0.060 (3)
H17A	0.3736	0.6213	0.6049	0.072*
H17B	0.3264	0.6931	0.5130	0.072*
C18	0.2957 (5)	0.5732 (11)	0.6514 (17)	0.066 (3)
H18A	0.3073	0.5037	0.6836	0.079*
H18B	0.2930	0.6116	0.7647	0.079*
C19	0.1509 (5)	0.4926 (10)	0.4628 (17)	0.061 (3)
H19A	0.1227	0.4469	0.5045	0.073*
H19B	0.1333	0.5575	0.4276	0.073*
C20	0.1968 (5)	0.5093 (10)	0.6158 (16)	0.060 (3)
H20A	0.1821	0.5443	0.7189	0.072*
H20B	0.2121	0.4438	0.6591	0.072*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0434 (6)	0.0455 (7)	0.0439 (7)	0.0000 (6)	0.0041 (5)	0.0023 (6)
Cl1	0.0561 (16)	0.0485 (15)	0.0583 (18)	0.0004 (12)	0.0004 (13)	0.0091 (13)
Cl2	0.070 (2)	0.071 (2)	0.112 (3)	0.0116 (17)	0.0176 (19)	−0.034 (2)
N1	0.045 (5)	0.045 (5)	0.056 (6)	−0.003 (4)	0.008 (4)	0.004 (4)
N2	0.048 (5)	0.044 (5)	0.056 (6)	−0.003 (4)	0.011 (4)	−0.003 (4)
N3	0.030 (4)	0.065 (6)	0.048 (5)	−0.005 (4)	−0.007 (4)	0.017 (4)
O1	0.056 (5)	0.056 (5)	0.095 (7)	−0.012 (4)	0.015 (5)	−0.008 (5)
O2	0.054 (5)	0.067 (5)	0.081 (6)	−0.002 (4)	0.003 (4)	0.005 (5)
O3	0.056 (5)	0.068 (6)	0.135 (9)	0.003 (5)	0.017 (5)	−0.004 (6)
O4	0.049 (5)	0.069 (6)	0.095 (7)	−0.016 (4)	0.009 (4)	−0.006 (5)
O5	0.061 (12)	0.068 (12)	0.22 (3)	−0.001 (10)	−0.028 (15)	0.059 (16)
C1	0.067 (7)	0.075 (8)	0.044 (7)	−0.005 (6)	0.010 (6)	0.021 (6)
C2	0.052 (6)	0.063 (7)	0.055 (7)	−0.006 (6)	0.004 (5)	0.013 (6)
C3	0.066 (7)	0.039 (6)	0.061 (8)	0.002 (5)	0.002 (6)	0.000 (5)
C4	0.050 (6)	0.044 (6)	0.057 (7)	−0.011 (5)	0.003 (5)	0.009 (5)
C5	0.040 (6)	0.056 (7)	0.055 (7)	−0.001 (5)	0.012 (5)	0.009 (6)
C6	0.063 (7)	0.049 (7)	0.055 (7)	0.003 (6)	0.009 (6)	0.002 (6)
C7	0.064 (8)	0.060 (8)	0.058 (7)	−0.018 (6)	0.006 (6)	0.004 (6)
C8	0.056 (8)	0.077 (9)	0.092 (11)	−0.018 (7)	−0.004 (7)	0.004 (8)
C9	0.067 (7)	0.062 (7)	0.047 (7)	−0.006 (6)	0.012 (6)	0.004 (6)
C10	0.058 (7)	0.052 (7)	0.051 (7)	−0.011 (6)	0.000 (5)	0.004 (5)
C11	0.069 (8)	0.039 (6)	0.072 (8)	−0.009 (6)	−0.002 (6)	0.001 (6)
C12	0.047 (6)	0.059 (7)	0.060 (8)	0.000 (5)	0.002 (5)	0.004 (6)
C13	0.045 (6)	0.055 (7)	0.063 (8)	−0.009 (5)	−0.007 (5)	−0.007 (6)
C14	0.060 (7)	0.047 (6)	0.063 (8)	0.003 (6)	0.001 (6)	−0.003 (6)
C15	0.050 (6)	0.065 (8)	0.060 (8)	0.000 (6)	−0.002 (5)	−0.007 (6)
C16	0.052 (7)	0.078 (9)	0.077 (9)	−0.003 (7)	0.001 (6)	−0.007 (7)
C17	0.048 (6)	0.063 (7)	0.069 (8)	−0.002 (6)	0.002 (6)	−0.010 (6)
C18	0.055 (7)	0.089 (9)	0.051 (7)	−0.003 (7)	−0.011 (6)	−0.006 (7)
C19	0.049 (6)	0.073 (8)	0.063 (8)	−0.002 (6)	0.016 (6)	−0.001 (6)
C20	0.059 (7)	0.069 (8)	0.055 (7)	0.001 (6)	0.025 (6)	−0.002 (6)

Geometric parameters (Å, º) top

Zn1—Cl1	2.275 (3)	C4—C5	1.371 (15)
Zn1—Cl2	2.361 (3)	C5—C6	1.344 (15)
Zn1—N1	2.183 (8)	C6—C7	1.363 (16)
Zn1—N2	2.141 (8)	C6—H6	0.9300
Zn1—N3	2.121 (9)	C7—H7	0.9300
N1—C1	1.483 (13)	C8—H8A	0.9700
N1—C17	1.481 (14)	C8—H8B	0.9700
N1—H1	0.9100	C9—C10	1.512 (15)
N2—C19	1.468 (14)	C9—H9A	0.9700
N2—C9	1.497 (14)	C9—H9B	0.9700
N2—H2	0.9100	C10—C11	1.381 (16)
N3—C20	1.467 (13)	C10—C15	1.379 (16)
N3—C18	1.487 (13)	C11—C12	1.392 (16)
N3—H3	0.9100	C11—H11	0.9300
O1—C4	1.369 (13)	C12—C13	1.366 (16)
O1—C8	1.400 (15)	C13—C14	1.332 (16)
O2—C5	1.395 (13)	C14—C15	1.384 (16)
O2—C8	1.444 (16)	C14—H14	0.9300
O3—C12	1.385 (13)	C15—H15	0.9300
O3—C16	1.404 (15)	C16—H16A	0.9700
O4—C13	1.402 (13)	C16—H16B	0.9700
O4—C16	1.415 (15)	C17—C18	1.482 (17)
O5—H5A	0.8505	C17—H17A	0.9700
O5—H5B	0.8504	C17—H17B	0.9700
C1—C2	1.521 (16)	C18—H18A	0.9700
C1—H1A	0.9700	C18—H18B	0.9700
C1—H1B	0.9700	C19—C20	1.514 (16)
C2—C7	1.378 (17)	C19—H19A	0.9700
C2—C3	1.425 (16)	C19—H19B	0.9700
C3—C4	1.363 (15)	C20—H20A	0.9700
C3—H3A	0.9300	C20—H20B	0.9700

N3—Zn1—N2	80.2 (3)	O2—C8—H8A	110.3
N3—Zn1—N1	79.8 (3)	O1—C8—H8B	110.3
N2—Zn1—N1	148.0 (3)	O2—C8—H8B	110.3
N3—Zn1—Cl1	106.6 (3)	H8A—C8—H8B	108.6
N2—Zn1—Cl1	104.6 (3)	N2—C9—C10	114.9 (9)
N1—Zn1—Cl1	104.9 (2)	N2—C9—H9A	108.5
N3—Zn1—Cl2	141.0 (3)	C10—C9—H9A	108.5
N2—Zn1—Cl2	93.9 (3)	N2—C9—H9B	108.5
N1—Zn1—Cl2	86.1 (3)	C10—C9—H9B	108.5
Cl1—Zn1—Cl2	112.09 (14)	H9A—C9—H9B	107.5
C1—N1—C17	115.2 (9)	C11—C10—C15	120.8 (11)
C1—N1—Zn1	112.6 (7)	C11—C10—C9	119.6 (10)
C17—N1—Zn1	107.9 (6)	C15—C10—C9	119.6 (11)
C1—N1—H1	106.9	C10—C11—C12	117.1 (10)
C17—N1—H1	106.9	C10—C11—H11	121.4
Zn1—N1—H1	106.9	C12—C11—H11	121.4
C19—N2—C9	113.1 (9)	C13—C12—O3	111.3 (10)
C19—N2—Zn1	108.2 (7)	C13—C12—C11	120.8 (11)
C9—N2—Zn1	114.7 (7)	O3—C12—C11	127.8 (11)
C19—N2—H2	106.8	C14—C13—C12	122.1 (11)
C9—N2—H2	106.8	C14—C13—O4	129.6 (11)
Zn1—N2—H2	106.8	C12—C13—O4	108.3 (10)
C20—N3—C18	116.3 (9)	C13—C14—C15	118.7 (11)
C20—N3—Zn1	110.7 (7)	C13—C14—H14	120.6
C18—N3—Zn1	109.8 (7)	C15—C14—H14	120.6
C20—N3—H3	106.5	C10—C15—C14	120.4 (11)
C18—N3—H3	106.5	C10—C15—H15	119.8
Zn1—N3—H3	106.5	C14—C15—H15	119.8
C4—O1—C8	105.8 (9)	O3—C16—O4	110.1 (9)
C5—O2—C8	104.9 (9)	O3—C16—H16A	109.6
C12—O3—C16	104.6 (9)	O4—C16—H16A	109.6
C13—O4—C16	105.3 (9)	O3—C16—H16B	109.6
H5A—O5—H5B	108.5	O4—C16—H16B	109.6
N1—C1—C2	112.8 (9)	H16A—C16—H16B	108.1
N1—C1—H1A	109.0	C18—C17—N1	108.2 (10)
C2—C1—H1A	109.0	C18—C17—H17A	110.1
N1—C1—H1B	109.0	N1—C17—H17A	110.1
C2—C1—H1B	109.0	C18—C17—H17B	110.1
H1A—C1—H1B	107.8	N1—C17—H17B	110.1
C7—C2—C3	118.7 (10)	H17A—C17—H17B	108.4
C7—C2—C1	121.2 (11)	N3—C18—C17	108.3 (10)
C3—C2—C1	120.2 (11)	N3—C18—H18A	110.0
C4—C3—C2	117.1 (11)	C17—C18—H18A	110.0
C4—C3—H3A	121.5	N3—C18—H18B	110.0
C2—C3—H3A	121.5	C17—C18—H18B	110.0
C3—C4—O1	127.3 (11)	H18A—C18—H18B	108.4
C3—C4—C5	121.9 (10)	N2—C19—C20	108.1 (9)
O1—C4—C5	110.8 (9)	N2—C19—H19A	110.1
C6—C5—C4	121.6 (10)	C20—C19—H19A	110.1
C6—C5—O2	130.4 (10)	N2—C19—H19B	110.1
C4—C5—O2	107.9 (10)	C20—C19—H19B	110.1
C5—C6—C7	118.2 (11)	H19A—C19—H19B	108.4
C5—C6—H6	120.9	N3—C20—C19	108.0 (9)
C7—C6—H6	120.9	N3—C20—H20A	110.1
C6—C7—C2	122.5 (11)	C19—C20—H20A	110.1
C6—C7—H7	118.8	N3—C20—H20B	110.1
C2—C7—H7	118.8	C19—C20—H20B	110.1
O1—C8—O2	106.9 (10)	H20A—C20—H20B	108.4
O1—C8—H8A	110.3

N3—Zn1—N1—C1	−143.6 (8)	C4—C5—C6—C7	−1.3 (17)
N2—Zn1—N1—C1	164.1 (8)	O2—C5—C6—C7	−175.6 (11)
Cl1—Zn1—N1—C1	−39.0 (8)	C5—C6—C7—C2	−0.3 (18)
Cl2—Zn1—N1—C1	72.9 (8)	C3—C2—C7—C6	1.3 (18)
N3—Zn1—N1—C17	−15.4 (7)	C1—C2—C7—C6	−178.7 (11)
N2—Zn1—N1—C17	−67.7 (10)	C4—O1—C8—O2	18.4 (13)
Cl1—Zn1—N1—C17	89.3 (7)	C5—O2—C8—O1	−19.4 (13)
Cl2—Zn1—N1—C17	−158.9 (7)	C19—N2—C9—C10	−59.0 (13)
N3—Zn1—N2—C19	19.0 (7)	Zn1—N2—C9—C10	176.3 (8)
N1—Zn1—N2—C19	71.2 (10)	N2—C9—C10—C11	101.8 (13)
Cl1—Zn1—N2—C19	−85.8 (7)	N2—C9—C10—C15	−76.2 (14)
Cl2—Zn1—N2—C19	160.1 (7)	C15—C10—C11—C12	−2.1 (18)
N3—Zn1—N2—C9	146.3 (8)	C9—C10—C11—C12	179.9 (10)
N1—Zn1—N2—C9	−161.5 (7)	C16—O3—C12—C13	4.1 (14)
Cl1—Zn1—N2—C9	41.5 (8)	C16—O3—C12—C11	−176.9 (13)
Cl2—Zn1—N2—C9	−72.5 (7)	C10—C11—C12—C13	0.2 (18)
N2—Zn1—N3—C20	10.7 (7)	C10—C11—C12—O3	−178.7 (12)
N1—Zn1—N3—C20	−144.1 (8)	O3—C12—C13—C14	180.0 (11)
Cl1—Zn1—N3—C20	113.2 (7)	C11—C12—C13—C14	1 (2)
Cl2—Zn1—N3—C20	−73.4 (8)	O3—C12—C13—O4	−1.1 (14)
N2—Zn1—N3—C18	140.4 (8)	C11—C12—C13—O4	179.8 (11)
N1—Zn1—N3—C18	−14.4 (8)	C16—O4—C13—C14	176.4 (13)
Cl1—Zn1—N3—C18	−117.1 (7)	C16—O4—C13—C12	−2.4 (13)
Cl2—Zn1—N3—C18	56.2 (9)	C12—C13—C14—C15	−0.1 (19)
C17—N1—C1—C2	71.4 (13)	O4—C13—C14—C15	−178.8 (12)
Zn1—N1—C1—C2	−164.2 (8)	C11—C10—C15—C14	3.0 (19)
N1—C1—C2—C7	86.2 (14)	C9—C10—C15—C14	−179.1 (11)
N1—C1—C2—C3	−93.9 (13)	C13—C14—C15—C10	−1.8 (18)
C7—C2—C3—C4	−0.7 (17)	C12—O3—C16—O4	−5.6 (14)
C1—C2—C3—C4	179.4 (10)	C13—O4—C16—O3	5.0 (14)
C2—C3—C4—O1	178.0 (11)	C1—N1—C17—C18	169.6 (10)
C2—C3—C4—C5	−0.8 (17)	Zn1—N1—C17—C18	42.8 (11)
C8—O1—C4—C3	170.4 (12)	C20—N3—C18—C17	169.0 (10)
C8—O1—C4—C5	−10.7 (13)	Zn1—N3—C18—C17	42.4 (12)
C3—C4—C5—C6	1.9 (18)	N1—C17—C18—N3	−57.0 (13)
O1—C4—C5—C6	−177.1 (10)	C9—N2—C19—C20	−173.0 (9)
C3—C4—C5—O2	177.4 (10)	Zn1—N2—C19—C20	−44.8 (11)
O1—C4—C5—O2	−1.6 (13)	C18—N3—C20—C19	−163.9 (10)
C8—O2—C5—C6	−172.2 (12)	Zn1—N3—C20—C19	−37.8 (11)
C8—O2—C5—C4	12.8 (12)	N2—C19—C20—N3	55.1 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.91	2.37	3.216 (12)	155
N2—H2···O5	0.91	2.19	3.03 (2)	155
N3—H3···Cl1ⁱⁱ	0.91	2.58	3.459 (9)	162
O5—H5A···Cl2	0.85	2.25	3.10 (2)	173
O5—H5B···Cl2ⁱⁱⁱ	0.85	2.20	3.05 (2)	173
C8—H8B···Cl2^iv	0.97	2.74	3.713 (14)	175
C15—H15···O5	0.93	2.56	3.35 (2)	143
C20—H20B···O5ⁱⁱⁱ	0.97	2.50	3.44 (2)	164

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+3/2, z+1/2; (iii) x, −y+1/2, z+1/2; (iv) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[ZnCl₂(C₂₀H₂₅N₃O₄)]·0.5H₂O
M_r	516.71
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	24.042 (3), 13.0193 (18), 7.2678 (14)
β (°)	94.934 (2)
V (Å³)	2266.5 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.35
Crystal size (mm)	0.57 × 0.15 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.513, 0.855
No. of measured, independent and observed [I > 2σ(I)] reflections	11175, 4003, 2735
R_int	0.077
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.104, 0.277, 1.12
No. of reflections	4003
No. of parameters	280
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0881P)² + 21.9915P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.46, −0.58

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1997), SHELXTL.

Selected bond lengths (Å) top

Zn1—Cl1	2.275 (3)	Zn1—N2	2.141 (8)
Zn1—Cl2	2.361 (3)	Zn1—N3	2.121 (9)
Zn1—N1	2.183 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.91	2.37	3.216 (12)	155
N2—H2···O5	0.91	2.19	3.03 (2)	155
N3—H3···Cl1ⁱⁱ	0.91	2.58	3.459 (9)	162
O5—H5A···Cl2	0.85	2.25	3.10 (2)	173
O5—H5B···Cl2ⁱⁱⁱ	0.85	2.20	3.05 (2)	173
C8—H8B···Cl2^iv	0.97	2.74	3.713 (14)	175
C15—H15···O5	0.93	2.56	3.35 (2)	143
C20—H20B···O5ⁱⁱⁱ	0.97	2.50	3.44 (2)	164

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+3/2, z+1/2; (iii) x, −y+1/2, z+1/2; (iv) −x+1, y+1/2, −z+1/2.

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.

E-mail address*
Repeat e-mail address* (for error checking)

Format*	PDF (US $40)
	HTML (US $40)
	PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number (non-UK EC countries only)
Country*

Terms and conditions of use
Contact us

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page