[(Z)-1-Amino-2-cyano-2-(4,6-di-2-pyridyl­pyrimidin-2-yl)ethenolato]chlorido(N,N-dimethyl­formamide-κO)zinc(II)

Jian, F.; Du, M.

doi:10.1107/S1600536810017770

[(Z)-1-Amino-2-cyano-2-(4,6-di-2-pyridylpyrimidin-2-yl)ethenolato]chlorido(N,N-dimethylformamide-κO)zinc(II)

In the title complex, [Zn(C₁₇H₁₁N₆O)Cl(C₃H₇NO)], the Zn^II atom has a distorted square-pyramidal coordination formed by one Cl, two O and two N atoms. In the crystal structure, intermolecular N—H

Cl hydrogen bonds link molecules into centrosymmetric dimers, which are further assembled by π–π interactions [centroid–centroid distances = 3.809 (3) and 3.834 (3) Å] into layers parallel to the ab plane. The crystal packing exhibits also weak intermolecular C—H

Cl interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810017770/cv2708sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536810017770/cv2708Isup2.hkl Contains datablock I

CCDC reference: 781227

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Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.005 Å
R factor = 0.049
wR factor = 0.167
Data-to-parameter ratio = 17.1

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No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.71
PLAT420_ALERT_2_C D-H Without Acceptor       N6     -   H6B    ...          ?
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      33.00 A   3 
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          6
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         12
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density       1.52 eA-3
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         59

Alert level G
PLAT072_ALERT_2_G SHELXL First Parameter in WGHT Unusually Large.       0.10
PLAT371_ALERT_2_G Long   C(sp2)-C(sp1) Bond  C15    -   C16    ...       1.41 Ang.
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal  (x 10000)       3000 Deg.
PLAT164_ALERT_4_G Nr. of Refined C-H H-Atoms in Heavy-Atom Struct.          1
PLAT180_ALERT_4_G Check Cell Rounding: # of Values Ending with 0 =          3
PLAT380_ALERT_4_G Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C19

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

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

Comment top

Recently, self-assembly of specially designed metal complexes have attracted intense attention due to their fascinating molecular structures and crystal-packing motifs (Chi et al., 2008). Several metal complexes with ligands containig heterocyclic pyrimidine and pyridine units have been studied previously to explore the role of hydrogen bonding in supramolecular assemblies (Patroniak et al., 2005; Kovbasyuk et al., 2005). Herein, we report the crystal structure of the title compound (I).

In (I) (Fig. 1), the zinc(II) ion is coordinated by one O anion and two N atoms of (Z)-3-amino-2-(4,6-di(pyridin-2-yl)pyrimidin-2-yl)-3- hydroxyacrylonitrile ligand, one O atom from DMF (DMF = N,N-dimethylformamide) and one Cl^- anion, forming a distorted square-pyramidal geometry. The Zn—Cl distance of 2.2956 (12)Å is longer than the value of 2.212 (4) Å in ZnCl₂(2,9-dimethyl-1,10-phenanthroline) (Preston et al., 1969) and 2.209 (1)Å in ZnCl₂(C₆H₄N₃CH₂COPh)₂ (Jian et al., 2004). The Zn—O bond lengths of 1.996 (3) and 2.066 (2)Å, respectively, are shorter than those reported previously (Patroniak et al., 2003). The Zn—N bond lengths are 2.103 (3) and 2.106 (2) Å, respectively, which are in disagreement with the corresponding five-coordination Zn—N distances found in similar compounds (Patroniak et al., 2003; Chi et al., 2008 ). The N3—Zn1—N4 bite angle is 77.58 (10)°, which is narrower than that in {Zn[4,6-bis(2-pyridyl)-2-aminopyrimidine](OOCCH₃)₂} [78.40 (7)°, Chi et al., 2008].

The five-membered chelate ring N3/C8/C9/N4/Zn1 (P1) is fairly planar, the deviation of atom Zn1 from the weighted least-squares plane N3/C8/C9/N4 is 0.079 Å. The dihedral angles formed by P1 with the planes N3/C14/C15/C17/O1/Zn1(P2), N2/C6—C8/N3/C14(P3), N4/C9—C13(P4) and N1/C1—C5(P5) are 16.67, 9.93, 5.02 and 19.49°, respectively. The dihedral angles formed by P3 with P4 and P5 are 5.61 and 16.55°, respectively. The dihedral angle between P2 and P4 is 14.55°.

In the crystal structure, intermolecular N—H···Cl hydrogen bonds (Table 2) link molecules into centrosymmetric dimers, which are further assembled by π-π interactions (Table 1) into layers parallel to ab plane. The crystal packing exhibits also weak intermolecular C—H···Cl interactions (Table 2).

Related literature top

For general background concerning the self-assembly of metal complexes with organic ligands, see: Chi et al. (2008); Patroniak et al. (2005); Kovbasyuk et al. (2005). For related structures, see: Preston et al. (1969); Jian et al. (2004); Patroniak et al. (2003).

Experimental top

The title complex was prepared by the reaction of (Z)-3-amino-2-(4,6-di(pyridin-2-yl)pyrimidin-2-yl)-3-hydroxyacrylonitrile (3.16 g, 10 mmol) with Zinc dichloride (1.36 g, 10 mmol) in water solution at 353 K for four hours. Single crystals suitable for x-ray measurements were obtained by recrystallization from DMF at room temperature.

Structure description top

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software(Enraf–Nonius, 1989); data reduction: NRCVAX (Gabe et al., 1989); 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: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The structure of the title compound showing 50% probability displacement ellipsoids and the atom-numbering scheme.

[(Z)-1-Amino-2-cyano-2-(4,6-di-2-pyridylpyrimidin-2- yl)ethenolato]chlorido(N,N-dimethylformamide-κ>i>O)zinc(II) top

Crystal data top

[Zn(C₁₇H₁₁N₆O)Cl(C₃H₇NO)]	Z = 2
M_r = 489.23	F(000) = 500
Triclinic, P1	D_x = 1.509 Mg m⁻³
Hall symbol: -p 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5610 (17) Å	Cell parameters from 25 reflections
b = 11.250 (2) Å	θ = 4–14°
c = 12.259 (3) Å	µ = 1.30 mm⁻¹
α = 110.70 (3)°	T = 295 K
β = 91.36 (3)°	Block, red
γ = 101.37 (3)°	0.20 × 0.17 × 0.15 mm
V = 1077.1 (4) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.026
Radiation source: fine-focus sealed tube	θ_max = 27.5°, θ_min = 3.0°
Graphite monochromator	h = −10→11
ω scans	k = −14→14
10564 measured reflections	l = −15→15
4863 independent reflections	3 standard reflections every 100 reflections
4214 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.167	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.1038P)² + 0.732P] where P = (F_o² + 2F_c²)/3
4863 reflections	(Δ/σ)_max = 0.001
284 parameters	Δρ_max = 1.58 e Å⁻³
0 restraints	Δρ_min = −0.58 e Å⁻³

Crystal data top

[Zn(C₁₇H₁₁N₆O)Cl(C₃H₇NO)]	γ = 101.37 (3)°
M_r = 489.23	V = 1077.1 (4) Å³
Triclinic, P1	Z = 2
a = 8.5610 (17) Å	Mo Kα radiation
b = 11.250 (2) Å	µ = 1.30 mm⁻¹
c = 12.259 (3) Å	T = 295 K
α = 110.70 (3)°	0.20 × 0.17 × 0.15 mm
β = 91.36 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.026
10564 measured reflections	3 standard reflections every 100 reflections
4863 independent reflections	intensity decay: none
4214 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.167	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 1.58 e Å⁻³
4863 reflections	Δρ_min = −0.58 e Å⁻³
284 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.33598 (4)	0.22665 (3)	0.92885 (3)	0.03870 (16)
Cl1	0.17317 (10)	0.36222 (8)	1.02298 (8)	0.0497 (2)
O1	0.5618 (3)	0.3196 (3)	0.9911 (2)	0.0511 (6)
O2	0.3716 (3)	0.2649 (3)	0.7773 (2)	0.0542 (6)
N1	0.3389 (4)	−0.0424 (3)	1.3640 (3)	0.0566 (8)
N2	0.4266 (4)	0.0756 (3)	1.2026 (3)	0.0496 (7)
N3	0.3565 (3)	0.1094 (2)	1.0273 (2)	0.0328 (5)
N4	0.1814 (3)	0.0487 (3)	0.8275 (2)	0.0401 (6)
N5	0.7321 (5)	0.3459 (4)	1.3637 (3)	0.0727 (10)
N6	0.7680 (4)	0.4302 (3)	1.1244 (3)	0.0591 (8)
H6A	0.8020	0.4736	1.0811	0.071*
H6B	0.8209	0.4462	1.1904	0.071*
N7	0.4824 (4)	0.3814 (3)	0.6721 (3)	0.0499 (7)
C1	0.3016 (6)	−0.0996 (5)	1.4418 (4)	0.0646 (11)
H1B	0.3465	−0.0551	1.5189	0.078*
C2	0.2027 (5)	−0.2183 (5)	1.4156 (4)	0.0628 (10)
H2B	0.1794	−0.2530	1.4733	0.075*
C3	0.1376 (6)	−0.2861 (5)	1.3011 (4)	0.0655 (11)
H3A	0.0698	−0.3679	1.2799	0.079*
C4	0.1749 (5)	−0.2300 (4)	1.2179 (4)	0.0562 (9)
H4A	0.1348	−0.2746	1.1397	0.067*
C5	0.2727 (4)	−0.1070 (3)	1.2534 (3)	0.0417 (7)
C6	0.3068 (4)	−0.0356 (3)	1.1717 (3)	0.0375 (6)
C7	0.2136 (4)	−0.0771 (3)	1.0636 (3)	0.0377 (6)
H7A	0.1342	−0.1533	1.0386	0.045*
C8	0.2430 (3)	−0.0020 (3)	0.9955 (2)	0.0344 (6)
C9	0.1483 (3)	−0.0380 (3)	0.8802 (2)	0.0358 (6)
C10	0.0349 (4)	−0.1544 (3)	0.8286 (3)	0.0460 (7)
H10A	0.0137	−0.2141	0.8658	0.055*
C11	−0.0458 (5)	−0.1798 (4)	0.7204 (3)	0.0538 (9)
H11A	−0.1233	−0.2562	0.6850	0.065*
C12	−0.0105 (4)	−0.0919 (4)	0.6666 (3)	0.0526 (8)
H12A	−0.0620	−0.1085	0.5934	0.063*
C13	0.1019 (4)	0.0213 (4)	0.7218 (3)	0.0483 (8)
H13A	0.1242	0.0815	0.6852	0.058*
C14	0.4514 (3)	0.1485 (3)	1.1287 (2)	0.0354 (6)
C15	0.5791 (4)	0.2644 (3)	1.1610 (3)	0.0385 (6)
C16	0.6641 (4)	0.3068 (3)	1.2730 (3)	0.0448 (7)
C17	0.6313 (4)	0.3365 (3)	1.0886 (3)	0.0392 (6)
C18	0.4729 (4)	0.3546 (4)	0.7681 (3)	0.0460 (7)
C19	0.3704 (7)	0.3062 (5)	0.5696 (4)	0.0831 (15)
H19A	0.2953	0.2405	0.5858	0.125*
H19B	0.4275	0.2655	0.5053	0.125*
H19C	0.3140	0.3627	0.5496	0.125*
C20	0.6072 (6)	0.4868 (4)	0.6641 (4)	0.0608 (10)
H20A	0.6742	0.5285	0.7370	0.091*
H20B	0.5583	0.5493	0.6478	0.091*
H20C	0.6709	0.4516	0.6022	0.091*
H1	0.546 (5)	0.406 (4)	0.831 (4)	0.056 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0394 (2)	0.0427 (2)	0.0365 (2)	0.00096 (15)	0.00087 (14)	0.02205 (16)
Cl1	0.0495 (5)	0.0453 (4)	0.0573 (5)	0.0067 (3)	0.0090 (4)	0.0242 (4)
O1	0.0415 (12)	0.0654 (16)	0.0501 (13)	−0.0046 (11)	−0.0003 (10)	0.0344 (12)
O2	0.0582 (15)	0.0631 (16)	0.0436 (13)	−0.0035 (12)	0.0051 (11)	0.0313 (12)
N1	0.068 (2)	0.0629 (19)	0.0421 (15)	0.0026 (15)	−0.0026 (14)	0.0297 (14)
N2	0.0516 (16)	0.0552 (17)	0.0468 (15)	0.0107 (13)	0.0047 (12)	0.0251 (13)
N3	0.0365 (12)	0.0333 (11)	0.0290 (11)	0.0053 (9)	0.0033 (9)	0.0130 (9)
N4	0.0424 (13)	0.0445 (14)	0.0350 (13)	0.0048 (11)	0.0015 (10)	0.0191 (11)
N5	0.074 (2)	0.079 (3)	0.055 (2)	−0.0010 (19)	−0.0158 (17)	0.0238 (18)
N6	0.0483 (17)	0.0606 (19)	0.067 (2)	−0.0140 (14)	−0.0101 (14)	0.0364 (16)
N7	0.0607 (18)	0.0525 (16)	0.0411 (14)	0.0061 (13)	0.0101 (13)	0.0257 (12)
C1	0.079 (3)	0.077 (3)	0.046 (2)	0.009 (2)	0.0025 (18)	0.0359 (19)
C2	0.068 (2)	0.080 (3)	0.063 (2)	0.018 (2)	0.0154 (19)	0.052 (2)
C3	0.070 (3)	0.063 (2)	0.073 (3)	−0.003 (2)	0.000 (2)	0.046 (2)
C4	0.063 (2)	0.056 (2)	0.055 (2)	−0.0007 (17)	−0.0042 (17)	0.0341 (17)
C5	0.0447 (16)	0.0456 (17)	0.0432 (16)	0.0119 (13)	0.0056 (12)	0.0253 (13)
C6	0.0407 (15)	0.0404 (15)	0.0376 (15)	0.0112 (12)	0.0084 (12)	0.0202 (12)
C7	0.0402 (15)	0.0362 (14)	0.0373 (14)	0.0037 (11)	0.0035 (11)	0.0169 (12)
C8	0.0369 (14)	0.0351 (14)	0.0325 (13)	0.0080 (11)	0.0044 (11)	0.0137 (11)
C9	0.0342 (14)	0.0401 (15)	0.0333 (14)	0.0081 (11)	0.0044 (11)	0.0138 (11)
C10	0.0490 (18)	0.0418 (16)	0.0439 (17)	0.0021 (13)	−0.0014 (13)	0.0164 (13)
C11	0.0513 (19)	0.0502 (19)	0.0464 (18)	−0.0023 (15)	−0.0069 (15)	0.0092 (15)
C12	0.0515 (19)	0.062 (2)	0.0381 (17)	0.0084 (16)	−0.0079 (14)	0.0143 (15)
C13	0.0515 (19)	0.057 (2)	0.0364 (16)	0.0049 (15)	−0.0040 (13)	0.0217 (14)
C14	0.0358 (14)	0.0375 (14)	0.0354 (14)	0.0085 (11)	0.0046 (11)	0.0161 (11)
C15	0.0376 (14)	0.0402 (15)	0.0376 (15)	0.0041 (12)	0.0004 (11)	0.0164 (12)
C16	0.0436 (17)	0.0468 (17)	0.0401 (17)	0.0031 (13)	−0.0038 (13)	0.0153 (13)
C17	0.0332 (14)	0.0401 (15)	0.0434 (16)	0.0045 (11)	0.0018 (11)	0.0163 (13)
C18	0.0488 (18)	0.0525 (19)	0.0398 (16)	0.0079 (15)	0.0064 (13)	0.0223 (14)
C19	0.110 (4)	0.086 (3)	0.048 (2)	−0.009 (3)	−0.012 (2)	0.036 (2)
C20	0.075 (3)	0.058 (2)	0.061 (2)	0.0138 (19)	0.027 (2)	0.0358 (18)

Geometric parameters (Å, º) top

Zn1—O1	1.996 (3)	C3—H3A	0.9300
Zn1—O2	2.066 (2)	C4—C5	1.380 (5)
Zn1—N4	2.103 (3)	C4—H4A	0.9300
Zn1—N3	2.106 (2)	C5—C6	1.491 (4)
Zn1—Cl1	2.2956 (12)	C6—C7	1.406 (4)
O1—C17	1.256 (4)	C7—C8	1.378 (4)
O2—C18	1.234 (4)	C7—H7A	0.9300
N1—C1	1.338 (5)	C8—C9	1.493 (4)
N1—C5	1.339 (5)	C9—C10	1.394 (4)
N2—C6	1.378 (4)	C10—C11	1.388 (5)
N2—C14	1.416 (4)	C10—H10A	0.9300
N3—C8	1.350 (4)	C11—C12	1.362 (6)
N3—C14	1.350 (4)	C11—H11A	0.9300
N4—C9	1.339 (4)	C12—C13	1.372 (5)
N4—C13	1.353 (4)	C12—H12A	0.9300
N5—C16	1.136 (5)	C13—H13A	0.9300
N6—C17	1.355 (4)	C14—C15	1.451 (4)
N6—H6A	0.8600	C15—C16	1.413 (4)
N6—H6B	0.8600	C15—C17	1.426 (4)
N7—C18	1.314 (4)	C18—H1	0.91 (4)
N7—C19	1.444 (6)	C19—H19A	0.9600
N7—C20	1.465 (5)	C19—H19B	0.9600
C1—C2	1.357 (6)	C19—H19C	0.9600
C1—H1B	0.9300	C20—H20A	0.9600
C2—C3	1.379 (6)	C20—H20B	0.9600
C2—H2B	0.9300	C20—H20C	0.9600
C3—C4	1.389 (5)

Cg1···Cg1ⁱ	3.809 (3)	Cg1···Cg2ⁱⁱ	3.834 (3)

O1—Zn1—O2	89.37 (11)	C8—C7—H7A	120.9
O1—Zn1—N4	146.12 (12)	C6—C7—H7A	120.9
O2—Zn1—N4	88.67 (11)	N3—C8—C7	123.4 (3)
O1—Zn1—N3	87.29 (10)	N3—C8—C9	114.8 (3)
O2—Zn1—N3	149.32 (11)	C7—C8—C9	121.8 (3)
N4—Zn1—N3	77.58 (10)	N4—C9—C10	121.5 (3)
O1—Zn1—Cl1	107.51 (9)	N4—C9—C8	115.4 (3)
O2—Zn1—Cl1	103.78 (9)	C10—C9—C8	123.1 (3)
N4—Zn1—Cl1	105.79 (8)	C11—C10—C9	118.8 (3)
N3—Zn1—Cl1	106.30 (7)	C11—C10—H10A	120.6
C17—O1—Zn1	126.9 (2)	C9—C10—H10A	120.6
C18—O2—Zn1	125.8 (2)	C12—C11—C10	119.5 (3)
C1—N1—C5	117.3 (3)	C12—C11—H11A	120.3
C6—N2—C14	120.6 (3)	C10—C11—H11A	120.3
C8—N3—C14	119.3 (2)	C11—C12—C13	119.2 (3)
C8—N3—Zn1	114.61 (19)	C11—C12—H12A	120.4
C14—N3—Zn1	124.8 (2)	C13—C12—H12A	120.4
C9—N4—C13	118.6 (3)	N4—C13—C12	122.5 (3)
C9—N4—Zn1	115.2 (2)	N4—C13—H13A	118.8
C13—N4—Zn1	125.8 (2)	C12—C13—H13A	118.8
C17—N6—H6A	120.0	N3—C14—N2	119.8 (3)
C17—N6—H6B	120.0	N3—C14—C15	119.9 (3)
H6A—N6—H6B	120.0	N2—C14—C15	120.3 (3)
C18—N7—C19	120.9 (3)	C16—C15—C17	116.8 (3)
C18—N7—C20	121.7 (3)	C16—C15—C14	117.0 (3)
C19—N7—C20	117.4 (3)	C17—C15—C14	126.1 (3)
N1—C1—C2	124.4 (4)	N5—C16—C15	177.3 (4)
N1—C1—H1B	117.8	O1—C17—N6	115.8 (3)
C2—C1—H1B	117.8	O1—C17—C15	125.4 (3)
C1—C2—C3	118.3 (4)	N6—C17—C15	118.9 (3)
C1—C2—H2B	120.9	O2—C18—N7	123.6 (3)
C3—C2—H2B	120.9	O2—C18—H1	119 (3)
C2—C3—C4	118.8 (4)	N7—C18—H1	117 (3)
C2—C3—H3A	120.6	N7—C19—H19A	109.5
C4—C3—H3A	120.6	N7—C19—H19B	109.5
C5—C4—C3	118.8 (4)	H19A—C19—H19B	109.5
C5—C4—H4A	120.6	N7—C19—H19C	109.5
C3—C4—H4A	120.6	H19A—C19—H19C	109.5
N1—C5—C4	122.3 (3)	H19B—C19—H19C	109.5
N1—C5—C6	115.6 (3)	N7—C20—H20A	109.5
C4—C5—C6	122.0 (3)	N7—C20—H20B	109.5
N2—C6—C7	118.5 (3)	H20A—C20—H20B	109.5
N2—C6—C5	120.6 (3)	N7—C20—H20C	109.5
C7—C6—C5	120.8 (3)	H20A—C20—H20C	109.5
C8—C7—C6	118.3 (3)	H20B—C20—H20C	109.5

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···Cl1ⁱⁱⁱ	0.86	2.57	3.396 (4)	161
C10—H10A···Cl1^iv	0.93	2.80	3.670 (4)	156

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

Experimental details

Crystal data
Chemical formula	[Zn(C₁₇H₁₁N₆O)Cl(C₃H₇NO)]
M_r	489.23
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	8.5610 (17), 11.250 (2), 12.259 (3)
α, β, γ (°)	110.70 (3), 91.36 (3), 101.37 (3)
V (Å³)	1077.1 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.30
Crystal size (mm)	0.20 × 0.17 × 0.15

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10564, 4863, 4214
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.167, 1.09
No. of reflections	4863
No. of parameters	284
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.58, −0.58

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), CAD-4 Software(Enraf–Nonius, 1989), NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), WinGX (Farrugia, 1999).

Selected interatomic distances (Å) top

Cg1···Cg1ⁱ

3.809 (3)

Cg1···Cg2ⁱⁱ

3.834 (3)