Bis{2-eth­oxy-6-[2-(methyl­ammonio)ethyl­imino­meth­yl]phenolato}thio­cyanato­zinc(II) nitrate

Wang, C.-Y.; Han, Z.-P.; Wu, X.; Yuan, C.-J.; Zhou, J.-B.

doi:10.1107/S1600536810000036

Bis{2-ethoxy-6-[2-(methylammonio)ethyliminomethyl]phenolato}thiocyanatozinc(II) nitrate

C.-Y. Wang, Z.-P. Han, X. Wu, C.-J. Yuan and J.-B. Zhou

In the title compound, [Zn(NCS)(C₁₂H₁₈N₂O₂)₂]NO₃, the Zn^II ion is chelated by the phenolate O and imine N atoms from two zwitterionic Schiff base ligands and is also coordinated by the N atom of a thiocyanate ligand, giving a distorted trigonal-bipyramidal geometry. Intramolecular N—H

O hydrogen bonds are observed in the complex cation. The nitrate anions are linked to the complex cations through N—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810000036/ci5009sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536810000036/ci5009Isup2.hkl Contains datablock I

CCDC reference: 764982

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.008 Å
R factor = 0.059
wR factor = 0.157
Data-to-parameter ratio = 18.7

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.12
            Rint given   0.139
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.15 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.37 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         N6
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C5
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C8
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C25
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds (x 1000) Ang ..          7
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      53.00 A   3 
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         13
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors of          N5
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         48

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          6

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

As part of our investigations into novel urease inhibitors, we have synthesized the title compound, a new Zn^II complex. The compound consists of a mononuclear zinc(II) complex cation and a nitrate anion. The Zn atom is chelated by the phenolate O and imine N atoms from two Schiff base ligands, and is coordinated by the N atom from a thiocyanate ligand, forming a trigonal-bipyramid geometry (Fig. 1). The coordinate bond lengths (Table 1) and angles are typical and are comparable with those observed in other similar zinc(II) complexes (Zhang & Wang, 2007; Adams et al., 2003). The amine N atoms of the Schiff base ligands are protonated and take no part in the coordination to the Zn^II ion.

Related literature top

For related structures, see: Zhang & Wang (2007); Adams et al. (2003).

Experimental top

3-Ethoxysalicylaldehyde (0.2 mmol, 33.2 mg) and N-methylethane-1,2-diamine (0.2 mmol, 14.8 mg) were dissolved in MeOH (10 ml). The mixture was stirred at room temperature for 10 min to give a clear yellow solution. To this solution was added an aqueous solution (2 ml) of ammonium thiocyanate (0.2 mmol, 15.2 mg) and an aqueous solution (3 ml) of Zn(NO₃)₂.6H₂O (0.1 mmol, 29.0 mg) with stirring. The resulting mixture was stirred for another 10 min at room temperature. After keeping the filtrate in air for a week, colourless block-shaped crystals were formed at the bottom of the vessel.

Structure description top

For related structures, see: Zhang & Wang (2007); Adams et al. (2003).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The asymmetric unit of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.

Bis{2-ethoxy-6-[2-(methylammonio)ethyliminomethyl]phenolato}thiocyanatozinc(II) nitrate top

Crystal data top

[Zn(NCS)(C₁₂H₁₈N₂O₂)₂]NO₃	F(000) = 1320
M_r = 630.03	D_x = 1.329 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3892 reflections
a = 10.601 (2) Å	θ = 2.3–25.5°
b = 23.335 (3) Å	µ = 0.90 mm⁻¹
c = 13.749 (2) Å	T = 298 K
β = 112.218 (3)°	Block, colourless
V = 3148.6 (9) Å³	0.20 × 0.20 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	6818 independent reflections
Radiation source: fine-focus sealed tube	3644 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.139
ω scan	θ_max = 27.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.841, T_max = 0.856	k = −29→28
18443 measured reflections	l = −17→15

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.157	H-atom parameters constrained
S = 0.91	w = 1/[σ²(F_o²) + (0.0647P)²] where P = (F_o² + 2F_c²)/3
6818 reflections	(Δ/σ)_max = 0.001
365 parameters	Δρ_max = 0.69 e Å⁻³
6 restraints	Δρ_min = −0.63 e Å⁻³

Crystal data top

[Zn(NCS)(C₁₂H₁₈N₂O₂)₂]NO₃	V = 3148.6 (9) Å³
M_r = 630.03	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.601 (2) Å	µ = 0.90 mm⁻¹
b = 23.335 (3) Å	T = 298 K
c = 13.749 (2) Å	0.20 × 0.20 × 0.18 mm
β = 112.218 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	6818 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3644 reflections with I > 2σ(I)
T_min = 0.841, T_max = 0.856	R_int = 0.139
18443 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	6 restraints
wR(F²) = 0.157	H-atom parameters constrained
S = 0.91	Δρ_max = 0.69 e Å⁻³
6818 reflections	Δρ_min = −0.63 e Å⁻³
365 parameters

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
Zn1	0.89814 (4)	0.910567 (18)	0.15980 (3)	0.04957 (18)
N1	0.9386 (4)	0.99186 (14)	0.1129 (3)	0.0615 (9)
N2	0.7214 (3)	1.05264 (13)	0.1565 (2)	0.0540 (8)
H2A	0.7686	1.0855	0.1636	0.065*
H2B	0.7705	1.0288	0.2085	0.065*
N3	0.8674 (3)	0.82940 (12)	0.2138 (3)	0.0520 (8)
N4	1.1307 (3)	0.78461 (14)	0.2169 (3)	0.0644 (9)
H4A	1.1340	0.7610	0.2695	0.077*
H4B	1.1352	0.8208	0.2404	0.077*
N5	0.1534 (6)	0.6837 (2)	0.3942 (4)	0.1041 (16)
N6	0.7831 (4)	0.88758 (17)	0.0075 (3)	0.0770 (11)
O1	1.0989 (3)	0.89846 (11)	0.2324 (2)	0.0599 (7)
O2	1.3351 (3)	0.86419 (17)	0.3710 (3)	0.0830 (10)
O3	0.8145 (3)	0.94858 (10)	0.24990 (18)	0.0515 (6)
O4	0.8062 (3)	1.02305 (12)	0.3908 (2)	0.0574 (7)
O5	0.1139 (4)	0.73228 (16)	0.4024 (3)	0.1062 (12)
O6	0.2187 (7)	0.6552 (2)	0.4726 (4)	0.175 (2)
O7	0.1510 (4)	0.66460 (16)	0.3124 (3)	0.1077 (13)
S1	0.65759 (17)	0.81681 (6)	−0.16349 (11)	0.1041 (5)
C1	1.1809 (5)	0.9943 (2)	0.2309 (4)	0.0709 (13)
C2	1.1969 (4)	0.9368 (2)	0.2642 (3)	0.0609 (11)
C3	1.3288 (5)	0.9196 (3)	0.3372 (4)	0.0748 (14)
C4	1.4340 (6)	0.9584 (3)	0.3697 (5)	0.106 (2)
H4	1.5196	0.9468	0.4160	0.128*
C5	1.4143 (8)	1.0148 (4)	0.3344 (5)	0.124 (3)
H5	1.4868	1.0405	0.3576	0.149*
C6	1.2928 (7)	1.0325 (3)	0.2677 (4)	0.0959 (19)
H6	1.2814	1.0704	0.2451	0.115*
C7	1.0547 (6)	1.01704 (19)	0.1556 (4)	0.0741 (14)
H7	1.0579	1.0549	0.1353	0.089*
C8	0.8286 (5)	1.0229 (2)	0.0317 (4)	0.0824 (15)
H8A	0.8086	1.0040	−0.0353	0.099*
H8B	0.8593	1.0615	0.0261	0.099*
C9	0.7009 (5)	1.02618 (19)	0.0535 (3)	0.0665 (12)
H9A	0.6336	1.0483	−0.0017	0.080*
H9B	0.6648	0.9878	0.0516	0.080*
C10	0.5889 (4)	1.0648 (2)	0.1656 (4)	0.0857 (15)
H10A	0.5390	1.0922	0.1130	0.128*
H10B	0.6047	1.0801	0.2341	0.128*
H10C	0.5372	1.0300	0.1557	0.128*
C11	1.4620 (5)	0.8444 (3)	0.4510 (5)	0.116 (2)
H11A	1.4898	0.8705	0.5102	0.139*
H11B	1.5329	0.8439	0.4225	0.139*
C12	1.4452 (7)	0.7866 (3)	0.4864 (6)	0.146 (3)
H12A	1.3661	0.7858	0.5045	0.219*
H12B	1.5243	0.7767	0.5468	0.219*
H12C	1.4340	0.7597	0.4310	0.219*
C13	0.8233 (3)	0.86814 (17)	0.3627 (3)	0.0508 (9)
C14	0.8163 (3)	0.92729 (16)	0.3392 (3)	0.0464 (9)
C15	0.8116 (3)	0.96620 (18)	0.4179 (3)	0.0505 (10)
C16	0.8127 (4)	0.9463 (2)	0.5121 (3)	0.0671 (12)
H16	0.8114	0.9721	0.5632	0.081*
C17	0.8156 (5)	0.8877 (2)	0.5319 (4)	0.0801 (14)
H17	0.8150	0.8747	0.5957	0.096*
C18	0.8192 (4)	0.8498 (2)	0.4591 (4)	0.0695 (12)
H18	0.8190	0.8108	0.4728	0.083*
C19	0.8394 (4)	0.82363 (17)	0.2956 (3)	0.0559 (10)
H19	0.8281	0.7862	0.3143	0.067*
C20	0.8790 (4)	0.77626 (17)	0.1597 (4)	0.0689 (12)
H20A	0.7965	0.7712	0.0977	0.083*
H20B	0.8866	0.7439	0.2059	0.083*
C21	0.9995 (4)	0.77629 (18)	0.1273 (3)	0.0670 (12)
H21A	1.0022	0.7402	0.0933	0.080*
H21B	0.9881	0.8066	0.0764	0.080*
C22	1.2507 (5)	0.7733 (2)	0.1879 (4)	0.0896 (15)
H22A	1.2468	0.7346	0.1632	0.134*
H22B	1.3331	0.7787	0.2484	0.134*
H22C	1.2494	0.7993	0.1334	0.134*
C23	0.8179 (4)	1.0643 (2)	0.4712 (3)	0.0668 (12)
H23A	0.9029	1.0586	0.5306	0.080*
H23B	0.7435	1.0594	0.4952	0.080*
C24	0.8139 (5)	1.1231 (2)	0.4286 (4)	0.0909 (16)
H24A	0.8793	1.1261	0.3960	0.136*
H24B	0.8354	1.1504	0.4847	0.136*
H24C	0.7244	1.1308	0.3775	0.136*
C25	0.7319 (5)	0.85823 (19)	−0.0634 (4)	0.0663 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0578 (3)	0.0483 (3)	0.0503 (3)	−0.0002 (2)	0.0291 (2)	−0.0045 (2)
N1	0.088 (3)	0.054 (2)	0.067 (2)	0.003 (2)	0.057 (2)	0.0022 (18)
N2	0.061 (2)	0.0538 (19)	0.0544 (19)	0.0034 (16)	0.0300 (17)	−0.0049 (16)
N3	0.0515 (19)	0.0462 (18)	0.060 (2)	−0.0018 (15)	0.0231 (17)	−0.0066 (16)
N4	0.074 (2)	0.057 (2)	0.065 (2)	0.0096 (18)	0.029 (2)	−0.0055 (18)
N5	0.161 (5)	0.073 (3)	0.075 (3)	0.019 (3)	0.040 (3)	0.017 (3)
N6	0.094 (3)	0.071 (2)	0.058 (2)	0.009 (2)	0.020 (2)	−0.007 (2)
O1	0.0493 (16)	0.0565 (16)	0.0770 (19)	−0.0063 (12)	0.0276 (15)	−0.0131 (14)
O2	0.0466 (18)	0.117 (3)	0.082 (2)	0.0016 (18)	0.0202 (17)	−0.016 (2)
O3	0.0676 (17)	0.0498 (15)	0.0483 (14)	0.0008 (13)	0.0346 (13)	0.0014 (12)
O4	0.0657 (18)	0.0639 (18)	0.0540 (16)	−0.0044 (14)	0.0355 (14)	−0.0120 (14)
O5	0.152 (3)	0.074 (2)	0.105 (3)	0.027 (2)	0.063 (3)	0.007 (2)
O6	0.280 (5)	0.103 (3)	0.127 (3)	0.022 (3)	0.057 (3)	0.006 (3)
O7	0.158 (4)	0.098 (3)	0.081 (2)	0.029 (2)	0.061 (3)	0.000 (2)
S1	0.1313 (13)	0.0791 (9)	0.0851 (9)	0.0145 (8)	0.0218 (9)	−0.0306 (8)
C1	0.093 (4)	0.082 (3)	0.064 (3)	−0.037 (3)	0.059 (3)	−0.028 (3)
C2	0.064 (3)	0.074 (3)	0.063 (3)	−0.021 (2)	0.046 (2)	−0.025 (2)
C3	0.057 (3)	0.114 (4)	0.068 (3)	−0.027 (3)	0.040 (3)	−0.031 (3)
C4	0.076 (4)	0.180 (7)	0.077 (4)	−0.052 (4)	0.046 (3)	−0.033 (4)
C5	0.124 (6)	0.189 (8)	0.086 (4)	−0.103 (6)	0.069 (4)	−0.050 (5)
C6	0.131 (5)	0.108 (4)	0.081 (4)	−0.071 (4)	0.075 (4)	−0.031 (3)
C7	0.123 (4)	0.052 (3)	0.086 (3)	−0.013 (3)	0.084 (4)	−0.010 (3)
C8	0.125 (4)	0.071 (3)	0.077 (3)	0.025 (3)	0.067 (3)	0.017 (3)
C9	0.084 (3)	0.067 (3)	0.052 (2)	0.016 (2)	0.030 (2)	−0.007 (2)
C10	0.068 (3)	0.116 (4)	0.081 (3)	0.021 (3)	0.037 (3)	−0.012 (3)
C11	0.057 (3)	0.181 (7)	0.100 (4)	0.009 (4)	0.018 (3)	−0.027 (5)
C12	0.107 (5)	0.160 (7)	0.141 (6)	0.053 (5)	0.012 (5)	0.010 (6)
C13	0.038 (2)	0.064 (3)	0.054 (2)	0.0025 (18)	0.0217 (18)	0.010 (2)
C14	0.0313 (19)	0.062 (2)	0.050 (2)	−0.0002 (17)	0.0201 (17)	−0.0017 (19)
C15	0.036 (2)	0.073 (3)	0.049 (2)	0.0034 (18)	0.0226 (18)	−0.001 (2)
C16	0.059 (3)	0.102 (4)	0.046 (2)	0.011 (2)	0.026 (2)	0.002 (2)
C17	0.078 (3)	0.117 (4)	0.057 (3)	0.028 (3)	0.038 (3)	0.030 (3)
C18	0.064 (3)	0.080 (3)	0.072 (3)	0.021 (2)	0.034 (2)	0.030 (3)
C19	0.046 (2)	0.050 (2)	0.069 (3)	−0.0051 (18)	0.020 (2)	0.009 (2)
C20	0.076 (3)	0.047 (2)	0.084 (3)	−0.008 (2)	0.030 (3)	−0.014 (2)
C21	0.079 (3)	0.052 (2)	0.072 (3)	0.003 (2)	0.031 (3)	−0.020 (2)
C22	0.084 (3)	0.098 (4)	0.099 (4)	0.014 (3)	0.049 (3)	−0.020 (3)
C23	0.053 (3)	0.089 (3)	0.060 (3)	−0.002 (2)	0.023 (2)	−0.026 (3)
C24	0.104 (4)	0.082 (4)	0.105 (4)	−0.024 (3)	0.060 (3)	−0.040 (3)
C25	0.078 (3)	0.061 (3)	0.059 (3)	0.018 (2)	0.024 (2)	0.001 (2)

Geometric parameters (Å, º) top

Zn1—O3	1.985 (2)	C8—C9	1.495 (6)
Zn1—O1	1.999 (3)	C8—H8A	0.97
Zn1—N6	2.056 (4)	C8—H8B	0.97
Zn1—N1	2.100 (3)	C9—H9A	0.97
Zn1—N3	2.104 (3)	C9—H9B	0.97
N1—C7	1.288 (6)	C10—H10A	0.96
N1—C8	1.465 (5)	C10—H10B	0.96
N2—C9	1.484 (5)	C10—H10C	0.96
N2—C10	1.485 (5)	C11—C12	1.466 (8)
N2—H2A	0.90	C11—H11A	0.97
N2—H2B	0.90	C11—H11B	0.97
N3—C19	1.274 (5)	C12—H12A	0.96
N3—C20	1.475 (5)	C12—H12B	0.96
N4—C21	1.481 (5)	C12—H12C	0.96
N4—C22	1.494 (5)	C13—C18	1.410 (6)
N4—H4A	0.90	C13—C14	1.413 (5)
N4—H4B	0.90	C13—C19	1.442 (5)
N5—O7	1.201 (5)	C14—C15	1.428 (5)
N5—O5	1.229 (5)	C15—C16	1.373 (5)
N5—O6	1.232 (6)	C16—C17	1.392 (6)
N6—C25	1.147 (5)	C16—H16	0.93
O1—C2	1.315 (4)	C17—C18	1.347 (6)
O2—C3	1.368 (6)	C17—H17	0.93
O2—C11	1.454 (6)	C18—H18	0.93
O3—C14	1.318 (4)	C19—H19	0.93
O4—C15	1.373 (5)	C20—C21	1.504 (6)
O4—C23	1.435 (4)	C20—H20A	0.97
S1—C25	1.621 (5)	C20—H20B	0.97
C1—C2	1.407 (6)	C21—H21A	0.97
C1—C6	1.416 (6)	C21—H21B	0.97
C1—C7	1.448 (7)	C22—H22A	0.96
C2—C3	1.435 (6)	C22—H22B	0.96
C3—C4	1.373 (7)	C22—H22C	0.96
C4—C5	1.392 (9)	C23—C24	1.486 (6)
C4—H4	0.93	C23—H23A	0.97
C5—C6	1.334 (9)	C23—H23B	0.97
C5—H5	0.93	C24—H24A	0.96
C6—H6	0.93	C24—H24B	0.96
C7—H7	0.93	C24—H24C	0.96

O3—Zn1—O1	113.20 (11)	N2—C10—H10B	109.5
O3—Zn1—N6	121.28 (14)	H10A—C10—H10B	109.5
O1—Zn1—N6	125.52 (14)	N2—C10—H10C	109.5
O3—Zn1—N1	88.83 (11)	H10A—C10—H10C	109.5
O1—Zn1—N1	88.76 (13)	H10B—C10—H10C	109.5
N6—Zn1—N1	91.96 (15)	O2—C11—C12	110.4 (5)
O3—Zn1—N3	90.95 (11)	O2—C11—H11A	109.6
O1—Zn1—N3	88.52 (11)	C12—C11—H11A	109.6
N6—Zn1—N3	90.76 (14)	O2—C11—H11B	109.6
N1—Zn1—N3	176.95 (14)	C12—C11—H11B	109.6
C7—N1—C8	118.1 (4)	H11A—C11—H11B	108.1
C7—N1—Zn1	122.9 (3)	C11—C12—H12A	109.5
C8—N1—Zn1	119.0 (3)	C11—C12—H12B	109.5
C9—N2—C10	111.0 (3)	H12A—C12—H12B	109.5
C9—N2—H2A	109.4	C11—C12—H12C	109.5
C10—N2—H2A	109.4	H12A—C12—H12C	109.5
C9—N2—H2B	109.4	H12B—C12—H12C	109.5
C10—N2—H2B	109.4	C18—C13—C14	119.6 (4)
H2A—N2—H2B	108.0	C18—C13—C19	115.9 (4)
C19—N3—C20	116.6 (3)	C14—C13—C19	124.5 (4)
C19—N3—Zn1	121.7 (3)	O3—C14—C13	124.2 (3)
C20—N3—Zn1	121.7 (3)	O3—C14—C15	118.3 (3)
C21—N4—C22	112.4 (3)	C13—C14—C15	117.5 (4)
C21—N4—H4A	109.1	C16—C15—O4	124.6 (4)
C22—N4—H4A	109.1	C16—C15—C14	120.6 (4)
C21—N4—H4B	109.1	O4—C15—C14	114.8 (3)
C22—N4—H4B	109.1	C15—C16—C17	120.6 (4)
H4A—N4—H4B	107.9	C15—C16—H16	119.7
O7—N5—O5	122.7 (5)	C17—C16—H16	119.7
O7—N5—O6	115.1 (5)	C18—C17—C16	120.3 (4)
O5—N5—O6	121.1 (5)	C18—C17—H17	119.9
C25—N6—Zn1	158.4 (4)	C16—C17—H17	119.9
C2—O1—Zn1	128.9 (3)	C17—C18—C13	121.3 (4)
C3—O2—C11	118.1 (4)	C17—C18—H18	119.4
C14—O3—Zn1	124.1 (2)	C13—C18—H18	119.4
C15—O4—C23	117.2 (3)	N3—C19—C13	127.7 (4)
C2—C1—C6	120.2 (5)	N3—C19—H19	116.1
C2—C1—C7	123.2 (4)	C13—C19—H19	116.1
C6—C1—C7	116.6 (5)	N3—C20—C21	113.0 (3)
O1—C2—C1	123.9 (4)	N3—C20—H20A	109.0
O1—C2—C3	118.8 (4)	C21—C20—H20A	109.0
C1—C2—C3	117.3 (4)	N3—C20—H20B	109.0
O2—C3—C4	125.6 (6)	C21—C20—H20B	109.0
O2—C3—C2	114.3 (4)	H20A—C20—H20B	107.8
C4—C3—C2	120.1 (6)	N4—C21—C20	112.9 (4)
C3—C4—C5	120.9 (6)	N4—C21—H21A	109.0
C3—C4—H4	119.6	C20—C21—H21A	109.0
C5—C4—H4	119.6	N4—C21—H21B	109.0
C6—C5—C4	120.8 (6)	C20—C21—H21B	109.0
C6—C5—H5	119.6	H21A—C21—H21B	107.8
C4—C5—H5	119.6	N4—C22—H22A	109.5
C5—C6—C1	120.8 (6)	N4—C22—H22B	109.5
C5—C6—H6	119.6	H22A—C22—H22B	109.5
C1—C6—H6	119.6	N4—C22—H22C	109.5
N1—C7—C1	128.6 (4)	H22A—C22—H22C	109.5
N1—C7—H7	115.7	H22B—C22—H22C	109.5
C1—C7—H7	115.7	O4—C23—C24	109.5 (3)
N1—C8—C9	113.2 (4)	O4—C23—H23A	109.8
N1—C8—H8A	108.9	C24—C23—H23A	109.8
C9—C8—H8A	108.9	O4—C23—H23B	109.8
N1—C8—H8B	108.9	C24—C23—H23B	109.8
C9—C8—H8B	108.9	H23A—C23—H23B	108.2
H8A—C8—H8B	107.8	C23—C24—H24A	109.5
N2—C9—C8	113.3 (4)	C23—C24—H24B	109.5
N2—C9—H9A	108.9	H24A—C24—H24B	109.5
C8—C9—H9A	108.9	C23—C24—H24C	109.5
N2—C9—H9B	108.9	H24A—C24—H24C	109.5
C8—C9—H9B	108.9	H24B—C24—H24C	109.5
H9A—C9—H9B	107.7	N6—C25—S1	179.2 (5)
N2—C10—H10A	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O3	0.90	1.96	2.750 (4)	145
N2—H2B···O4	0.90	2.39	3.078 (4)	133
N4—H4B···O1	0.90	1.85	2.697 (4)	157
N4—H4B···O2	0.90	2.42	3.027 (5)	125
N2—H2A···O7ⁱ	0.90	2.01	2.898 (5)	170
N2—H2A···O6ⁱ	0.90	2.52	3.183 (6)	131
N4—H4A···O5ⁱⁱ	0.90	2.03	2.894 (5)	160
N4—H4A···O7ⁱⁱ	0.90	2.31	3.066 (5)	141

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

Experimental details

Crystal data
Chemical formula	[Zn(NCS)(C₁₂H₁₈N₂O₂)₂]NO₃
M_r	630.03
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	10.601 (2), 23.335 (3), 13.749 (2)
β (°)	112.218 (3)
V (Å³)	3148.6 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.90
Crystal size (mm)	0.20 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.841, 0.856
No. of measured, independent and observed [I > 2σ(I)] reflections	18443, 6818, 3644
R_int	0.139
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.157, 0.91
No. of reflections	6818
No. of parameters	365
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.69, −0.63

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Zn1—O3	1.985 (2)	Zn1—N1	2.100 (3)
Zn1—O1	1.999 (3)	Zn1—N3	2.104 (3)
Zn1—N6	2.056 (4)