{Bis­[2-(3,5-dimethyl­pyrazol-1-yl)eth­yl]amine-κ2N,N′}dichloridozinc(II) methanol solvate

Lee, R.E.; Park, Y.D.; Jeong, J.H.

doi:10.1107/S1600536807048179

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{Bis[2-(3,5-dimethylpyrazol-1-yl)ethyl]amine-κ²N,N′}dichloridozinc(II) methanol solvate

R. E. Lee, Y. D. Park and J. H. Jeong

In the title compound, [ZnCl₂(C₁₄H₂₃N₅)]·CH₃OH, the Zn atom is coordinated by two N atoms and two Cl atoms in an approximately tetrahedral arrangement. The dihedral angle between the N—Zn—N and Cl—Zn—Cl planes is 89.69 (5)°. The methanol solvent molecule takes part in the formation of the hydrogen-bond system.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807048179/rk2043sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807048179/rk2043Isup2.hkl Contains datablock I

CCDC reference: 667128

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.028
wR factor = 0.082
Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT793_ALERT_1_G Check the Absolute Configuration of N3     = ...          R
PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn          (2)       1.93

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

The ligand, bis[2–(3,5–dimethylpyrazol–1–yl)ethyl]amine, synthesized (Sorrell & Malachowski, 1983) and its complex of cobalt, copper or zinc was reported (van Berkel et al., 1994). Nickel complex of the ligand was reported as an efficient catalyst for dimerization of enthylene to 1–butene (Ajellal et al., 2006). Aluminium and zinc alkyl complexes bearing the ligand were synthesized and show the activities on polymerization of methyl methacrylate and lactide (Lian et al., 2007). Also palladium complexes containing the ligand were reported (Pañella et al., 2006; Mendoza et al., 2006). In the title complex, the ligand acts as bidentate though it is a potential tridentate. However, the ligand was κ³ bonding mode at zinc from reaction ZnCl₂–to–ligand ratio of 2:1 (van Berkel et al., 1994). Herein, we report the crystal structure of Zn(II) complex containing bis[2–(3,5–dimethylpyrazol–1–yl)ethyl]amine as bidentate. The geometry around Zn(II) is an approximately tetrahedron. The dihedral angle between N—Zn—N and Cl—Zn—Cl planes is 89.69 (5)°.

The methanol solvate molecule takes part in the formation of H–bonds system: the hydroxo–group of one is a donor and acceptor in this system - see table of hydrogen–bond geometry.

Related literature top

For the synthesis of bis[2–(3,5–dimethylpyrazol–1–yl)ethyl]amine see: Sorrell & Malachowski, (1983). For related structures see: van Berkel et al. (1994); Ajellal et al. (2006); Pañella et al. (2006); Mendoza et al. (2006); Lian et al. (2007).

Experimental top

To bis{2–(3,5–dimethyl–1–pyrazolyl)ethyl}amine (1.67 g, 6.4 mmol) was added dropwise a solution of ZnCl₂ (0.87 g, 6.4 mmol) in methanol (20 ml). The mixture was stirred for 1 day at room temperature. The solvent was removed and the residue was washed with ether to give white solids. Colorless crystals was obtained from methanol solution. Yield; 1.63 g (64%). Anal. Calculated for C₁₅H₂₇Cl₂N₅OZn: C, 41.93; H, 6.33; N, 16.30. Found: C, 42.09; H, 6.24; N, 16.46%. ¹H NMR (DMSO–d₆); δ 5.97 (s, H-Pz), 4.20 (t, CH₂-Pz, J=6.0, 5.7 Hz), 3.07 (t, NCH₂–, J=5.7, 5.4 Hz), 2.25 (s, CH₃-Pz), 2.18 (s, CH₃-Pz), where Pz - pyrazolyl.

Structure description top

The methanol solvate molecule takes part in the formation of H–bonds system: the hydroxo–group of one is a donor and acceptor in this system - see table of hydrogen–bond geometry.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989; data reduction: XCAD (McArdle, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

Fig. 1. A view of the dichlorido{bis[2–(3,5–dimethylpyrazol–1–yl)ethyl]amine–κ²N,N'}zinc with the numbering scheme. Displacement ellipsoids are drawn at the 40% probability level. H atoms are drawn as a spheres with arbitrary radius.

{Bis[2-(3,5-dimethylpyrazol-1-yl)ethyl]amine- κ²N,N'}dichloridozinc(II) methanol solvate top

Crystal data top

[ZnCl₂(C₁₄H₂₃N₅)]·CH₄O	Z = 2
M_r = 429.71	F(000) = 448
Triclinic, P1	D_x = 1.411 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 9.3550 (6) Å	Cell parameters from 25 reflections
b = 9.3562 (4) Å	θ = 10.6–13.2°
c = 13.3177 (7) Å	µ = 1.49 mm⁻¹
α = 83.362 (4)°	T = 293 K
β = 72.448 (5)°	Block, colourless
γ = 65.563 (4)°	0.45 × 0.40 × 0.35 mm
V = 1011.77 (10) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	3209 reflections with I > 2σ(I)
Radiation source: Fine–focus sealed tube	R_int = 0.008
Graphite monochromator	θ_max = 25.5°, θ_min = 1.6°
Scintillation counter scans	h = 0→11
Absorption correction: ψ scan (ABSCALC; McArdle & Daly, 1999)	k = −10→11
T_min = 0.517, T_max = 0.594	l = −15→16
4135 measured reflections	3 standard reflections every 60 min
3753 independent reflections	intensity decay: 0.2%

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0529P)² + 0.1929P] where P = (F_o² + 2F_c²)/3
3753 reflections	(Δ/σ)_max < 0.001
225 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

[ZnCl₂(C₁₄H₂₃N₅)]·CH₄O	γ = 65.563 (4)°
M_r = 429.71	V = 1011.77 (10) Å³
Triclinic, P1	Z = 2
a = 9.3550 (6) Å	Mo Kα radiation
b = 9.3562 (4) Å	µ = 1.49 mm⁻¹
c = 13.3177 (7) Å	T = 293 K
α = 83.362 (4)°	0.45 × 0.40 × 0.35 mm
β = 72.448 (5)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	3209 reflections with I > 2σ(I)
Absorption correction: ψ scan (ABSCALC; McArdle & Daly, 1999)	R_int = 0.008
T_min = 0.517, T_max = 0.594	3 standard reflections every 60 min
4135 measured reflections	intensity decay: 0.2%
3753 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.38 e Å⁻³
3753 reflections	Δρ_min = −0.33 e Å⁻³
225 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Zn	0.50037 (3)	0.75209 (3)	0.161235 (17)	0.04246 (10)
Cl1	0.53380 (8)	0.54111 (7)	0.26152 (5)	0.06128 (16)
Cl2	0.27310 (8)	0.86417 (8)	0.10889 (5)	0.06388 (17)
N1	0.7028 (2)	0.7171 (2)	0.03740 (13)	0.0458 (4)
C1	0.7535 (3)	0.6476 (2)	−0.05640 (15)	0.0455 (4)
C2	0.6472 (3)	0.5905 (3)	−0.09021 (19)	0.0612 (6)
H2A	0.6768	0.4810	−0.0745	0.092*
H2B	0.6620	0.6053	−0.1646	0.092*
H2C	0.5348	0.6486	−0.0532	0.092*
C3	0.9078 (3)	0.6424 (2)	−0.10956 (16)	0.0480 (5)
H3	0.9703	0.5994	−0.1761	0.058*
C4	0.9508 (2)	0.7128 (2)	−0.04526 (15)	0.0426 (4)
C5	1.0994 (3)	0.7445 (3)	−0.06226 (18)	0.0572 (5)
H5A	1.0735	0.8541	−0.0760	0.086*
H5B	1.1834	0.6837	−0.1213	0.086*
H5C	1.1372	0.7163	−0.0004	0.086*
N2	0.8257 (2)	0.7571 (2)	0.04240 (12)	0.0435 (4)
C6	0.8102 (3)	0.8360 (3)	0.13570 (17)	0.0573 (6)
H6A	0.8966	0.8739	0.1202	0.069*
H6B	0.8250	0.7606	0.1921	0.069*
C7	0.6463 (3)	0.9729 (3)	0.17301 (18)	0.0551 (5)
H7A	0.6579	1.0460	0.2128	0.066*
H7B	0.6121	1.0276	0.1124	0.066*
N3	0.5195 (2)	0.9201 (2)	0.23970 (13)	0.0419 (4)
H3N	0.549 (3)	0.874 (3)	0.2914 (18)	0.039 (6)*
C8	0.3639 (3)	1.0539 (2)	0.28370 (16)	0.0469 (4)
H8A	0.3140	1.1054	0.2280	0.056*
H8B	0.3842	1.1296	0.3151	0.056*
C9	0.2496 (3)	0.9949 (3)	0.36641 (17)	0.0493 (5)
H9A	0.2168	0.9319	0.3324	0.059*
H9B	0.3074	0.9282	0.4151	0.059*
N4	0.1048 (2)	1.1224 (2)	0.42467 (13)	0.0476 (4)
N5	0.1135 (2)	1.1900 (2)	0.50638 (14)	0.0518 (4)
C10	−0.0371 (3)	1.2995 (3)	0.54475 (18)	0.0545 (5)
C11	−0.0740 (4)	1.3975 (4)	0.6380 (2)	0.0752 (8)
H11A	−0.1389	1.3647	0.6989	0.113*
H11B	−0.1332	1.5059	0.6244	0.113*
H11C	0.0266	1.3848	0.6503	0.113*
C12	−0.1397 (3)	1.3013 (3)	0.4873 (2)	0.0573 (6)
H12	−0.2497	1.3671	0.4984	0.069*
C13	−0.0471 (3)	1.1874 (3)	0.41129 (17)	0.0500 (5)
C14	−0.0908 (3)	1.1326 (3)	0.3282 (2)	0.0667 (6)
H14A	−0.0051	1.1154	0.2634	0.100*
H14B	−0.1911	1.2109	0.3180	0.100*
H14C	−0.1041	1.0363	0.3498	0.100*
C15	0.4334 (4)	0.2736 (4)	0.4990 (3)	0.0890 (9)
H151	0.3527	0.3363	0.4636	0.134*
H152	0.5311	0.2085	0.4486	0.134*
H153	0.4579	0.3410	0.5342	0.134*
O	0.3734 (3)	0.1799 (3)	0.57224 (17)	0.0806 (6)
H1O	0.306 (4)	0.161 (4)	0.561 (3)	0.081 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn	0.04342 (14)	0.04865 (15)	0.03929 (14)	−0.02289 (10)	−0.00885 (10)	−0.00452 (9)
Cl1	0.0659 (3)	0.0536 (3)	0.0568 (3)	−0.0239 (3)	−0.0080 (3)	0.0041 (2)
Cl2	0.0606 (3)	0.0711 (4)	0.0668 (4)	−0.0204 (3)	−0.0321 (3)	−0.0099 (3)
N1	0.0505 (9)	0.0558 (10)	0.0378 (8)	−0.0310 (8)	−0.0053 (7)	−0.0068 (7)
C1	0.0583 (12)	0.0434 (10)	0.0379 (10)	−0.0248 (9)	−0.0102 (9)	−0.0027 (8)
C2	0.0751 (16)	0.0703 (15)	0.0517 (13)	−0.0436 (13)	−0.0101 (11)	−0.0144 (11)
C3	0.0528 (11)	0.0489 (11)	0.0370 (10)	−0.0184 (9)	−0.0052 (9)	−0.0075 (8)
C4	0.0410 (10)	0.0439 (10)	0.0379 (9)	−0.0133 (8)	−0.0089 (8)	−0.0004 (8)
C5	0.0402 (11)	0.0761 (15)	0.0513 (12)	−0.0205 (10)	−0.0072 (9)	−0.0100 (11)
N2	0.0427 (9)	0.0531 (9)	0.0376 (8)	−0.0223 (7)	−0.0086 (7)	−0.0056 (7)
C6	0.0487 (12)	0.0872 (16)	0.0444 (11)	−0.0358 (11)	−0.0048 (9)	−0.0203 (11)
C7	0.0607 (13)	0.0643 (13)	0.0478 (11)	−0.0389 (11)	0.0015 (10)	−0.0180 (10)
N3	0.0440 (9)	0.0495 (9)	0.0341 (8)	−0.0211 (7)	−0.0085 (7)	−0.0038 (7)
C8	0.0506 (11)	0.0474 (11)	0.0410 (10)	−0.0201 (9)	−0.0075 (9)	−0.0055 (8)
C9	0.0449 (11)	0.0507 (11)	0.0452 (11)	−0.0157 (9)	−0.0076 (9)	0.0000 (9)
N4	0.0407 (9)	0.0569 (10)	0.0405 (9)	−0.0157 (8)	−0.0098 (7)	−0.0015 (7)
N5	0.0438 (9)	0.0649 (11)	0.0437 (9)	−0.0197 (8)	−0.0098 (8)	−0.0035 (8)
C10	0.0470 (11)	0.0623 (13)	0.0500 (12)	−0.0243 (10)	−0.0023 (9)	−0.0046 (10)
C11	0.0654 (16)	0.0877 (19)	0.0651 (16)	−0.0284 (14)	−0.0016 (13)	−0.0250 (14)
C12	0.0377 (10)	0.0615 (13)	0.0662 (14)	−0.0155 (10)	−0.0108 (10)	−0.0020 (11)
C13	0.0426 (11)	0.0608 (13)	0.0502 (12)	−0.0249 (10)	−0.0145 (9)	0.0077 (10)
C14	0.0623 (15)	0.0826 (17)	0.0657 (15)	−0.0330 (13)	−0.0271 (12)	0.0016 (13)
C15	0.091 (2)	0.102 (2)	0.098 (2)	−0.0493 (19)	−0.0520 (19)	0.0208 (19)
O	0.0804 (13)	0.1126 (17)	0.0730 (13)	−0.0492 (13)	−0.0461 (11)	0.0182 (11)

Geometric parameters (Å, º) top

Zn—N1	2.0349 (16)	N3—H3N	0.83 (2)
Zn—N3	2.0787 (17)	C8—C9	1.516 (3)
Zn—Cl1	2.2158 (6)	C8—H8A	0.9700
Zn—Cl2	2.2330 (6)	C8—H8B	0.9700
N1—C1	1.335 (2)	C9—N4	1.450 (3)
N1—N2	1.369 (2)	C9—H9A	0.9700
C1—C3	1.386 (3)	C9—H9B	0.9700
C1—C2	1.497 (3)	N4—C13	1.354 (3)
C2—H2A	0.9600	N4—N5	1.359 (3)
C2—H2B	0.9600	N5—C10	1.337 (3)
C2—H2C	0.9600	C10—C12	1.391 (3)
C3—C4	1.374 (3)	C10—C11	1.498 (3)
C3—H3	0.9300	C11—H11A	0.9600
C4—N2	1.338 (2)	C11—H11B	0.9600
C4—C5	1.485 (3)	C11—H11C	0.9600
C5—H5A	0.9600	C12—C13	1.366 (3)
C5—H5B	0.9600	C12—H12	0.9300
C5—H5C	0.9600	C13—C14	1.494 (3)
N2—C6	1.458 (3)	C14—H14A	0.9600
C6—C7	1.517 (3)	C14—H14B	0.9600
C6—H6A	0.9700	C14—H14C	0.9600
C6—H6B	0.9700	C15—O	1.383 (4)
C7—N3	1.479 (3)	C15—H151	0.9600
C7—H7A	0.9700	C15—H152	0.9600
C7—H7B	0.9700	C15—H153	0.9600
N3—C8	1.476 (3)	O—H1O	0.78 (3)

N1—Zn—N3	97.10 (6)	C8—N3—H3N	105.1 (15)
N1—Zn—Cl1	111.06 (5)	C7—N3—H3N	108.8 (15)
N3—Zn—Cl1	107.94 (5)	Zn—N3—H3N	104.9 (15)
N1—Zn—Cl2	110.94 (5)	N3—C8—C9	109.32 (17)
N3—Zn—Cl2	108.51 (5)	N3—C8—H8A	109.8
Cl1—Zn—Cl2	118.95 (3)	C9—C8—H8A	109.8
C1—N1—N2	105.84 (16)	N3—C8—H8B	109.8
C1—N1—Zn	132.04 (15)	C9—C8—H8B	109.8
N2—N1—Zn	121.97 (12)	H8A—C8—H8B	108.3
N1—C1—C3	109.52 (18)	N4—C9—C8	112.15 (18)
N1—C1—C2	120.74 (19)	N4—C9—H9A	109.2
C3—C1—C2	129.74 (19)	C8—C9—H9A	109.2
C1—C2—H2A	109.5	N4—C9—H9B	109.2
C1—C2—H2B	109.5	C8—C9—H9B	109.2
H2A—C2—H2B	109.5	H9A—C9—H9B	107.9
C1—C2—H2C	109.5	C13—N4—N5	111.80 (17)
H2A—C2—H2C	109.5	C13—N4—C9	129.17 (19)
H2B—C2—H2C	109.5	N5—N4—C9	119.02 (17)
C4—C3—C1	106.98 (17)	C10—N5—N4	105.05 (18)
C4—C3—H3	126.5	N5—C10—C12	110.4 (2)
C1—C3—H3	126.5	N5—C10—C11	119.9 (2)
N2—C4—C3	106.46 (18)	C12—C10—C11	129.6 (2)
N2—C4—C5	122.74 (19)	C10—C11—H11A	109.5
C3—C4—C5	130.78 (19)	C10—C11—H11B	109.5
C4—C5—H5A	109.5	H11A—C11—H11B	109.5
C4—C5—H5B	109.5	C10—C11—H11C	109.5
H5A—C5—H5B	109.5	H11A—C11—H11C	109.5
C4—C5—H5C	109.5	H11B—C11—H11C	109.5
H5A—C5—H5C	109.5	C13—C12—C10	106.5 (2)
H5B—C5—H5C	109.5	C13—C12—H12	126.7
C4—N2—N1	111.20 (16)	C10—C12—H12	126.7
C4—N2—C6	128.46 (17)	N4—C13—C12	106.2 (2)
N1—N2—C6	120.34 (16)	N4—C13—C14	122.7 (2)
N2—C6—C7	113.19 (19)	C12—C13—C14	131.1 (2)
N2—C6—H6A	108.9	C13—C14—H14A	109.5
C7—C6—H6A	108.9	C13—C14—H14B	109.5
N2—C6—H6B	108.9	H14A—C14—H14B	109.5
C7—C6—H6B	108.9	C13—C14—H14C	109.5
H6A—C6—H6B	107.8	H14A—C14—H14C	109.5
N3—C7—C6	111.62 (19)	H14B—C14—H14C	109.5
N3—C7—H7A	109.3	O—C15—H151	109.5
C6—C7—H7A	109.3	O—C15—H152	109.5
N3—C7—H7B	109.3	H151—C15—H152	109.5
C6—C7—H7B	109.3	O—C15—H153	109.5
H7A—C7—H7B	108.0	H151—C15—H153	109.5
C8—N3—C7	111.73 (17)	H152—C15—H153	109.5
C8—N3—Zn	114.97 (13)	C15—O—H1O	116 (2)
C7—N3—Zn	110.82 (12)

N3—Zn—N1—C1	−164.96 (19)	C6—C7—N3—C8	175.01 (17)
Cl1—Zn—N1—C1	82.7 (2)	C6—C7—N3—Zn	−55.4 (2)
Cl2—Zn—N1—C1	−52.0 (2)	N1—Zn—N3—C8	137.79 (14)
N3—Zn—N1—N2	20.20 (16)	Cl1—Zn—N3—C8	−107.31 (13)
Cl1—Zn—N1—N2	−92.17 (15)	Cl2—Zn—N3—C8	22.86 (15)
Cl2—Zn—N1—N2	133.17 (14)	N1—Zn—N3—C7	9.90 (16)
N2—N1—C1—C3	0.6 (2)	Cl1—Zn—N3—C7	124.80 (15)
Zn—N1—C1—C3	−174.84 (15)	Cl2—Zn—N3—C7	−105.03 (15)
N2—N1—C1—C2	−178.83 (19)	C7—N3—C8—C9	−169.66 (18)
Zn—N1—C1—C2	5.7 (3)	Zn—N3—C8—C9	62.9 (2)
N1—C1—C3—C4	−0.5 (2)	N3—C8—C9—N4	170.79 (17)
C2—C1—C3—C4	178.9 (2)	C8—C9—N4—C13	98.9 (3)
C1—C3—C4—N2	0.1 (2)	C8—C9—N4—N5	−82.3 (2)
C1—C3—C4—C5	−178.0 (2)	C13—N4—N5—C10	0.1 (2)
C3—C4—N2—N1	0.2 (2)	C9—N4—N5—C10	−178.89 (19)
C5—C4—N2—N1	178.60 (19)	N4—N5—C10—C12	−0.3 (3)
C3—C4—N2—C6	179.6 (2)	N4—N5—C10—C11	179.1 (2)
C5—C4—N2—C6	−2.1 (3)	N5—C10—C12—C13	0.3 (3)
C1—N1—N2—C4	−0.5 (2)	C11—C10—C12—C13	−179.0 (3)
Zn—N1—N2—C4	175.48 (13)	N5—N4—C13—C12	0.0 (2)
C1—N1—N2—C6	−179.9 (2)	C9—N4—C13—C12	178.9 (2)
Zn—N1—N2—C6	−3.9 (3)	N5—N4—C13—C14	−178.8 (2)
C4—N2—C6—C7	133.5 (2)	C9—N4—C13—C14	0.1 (4)
N1—N2—C6—C7	−47.2 (3)	C10—C12—C13—N4	−0.2 (3)
N2—C6—C7—N3	83.4 (2)	C10—C12—C13—C14	178.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O—H1O···N5ⁱ	0.78 (4)	2.04 (4)	2.787 (3)	159 (3)
N3—H3N···Oⁱⁱ	0.83 (3)	2.09 (2)	2.889 (3)	163 (2)

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

Experimental details

Crystal data
Chemical formula	[ZnCl₂(C₁₄H₂₃N₅)]·CH₄O
M_r	429.71
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.3550 (6), 9.3562 (4), 13.3177 (7)
α, β, γ (°)	83.362 (4), 72.448 (5), 65.563 (4)
V (Å³)	1011.77 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.49
Crystal size (mm)	0.45 × 0.40 × 0.35

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan (ABSCALC; McArdle & Daly, 1999)
T_min, T_max	0.517, 0.594
No. of measured, independent and observed [I > 2σ(I)] reflections	4135, 3753, 3209
R_int	0.008
(sin θ/λ)_max (Å⁻¹)	0.605

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.082, 1.04
No. of reflections	3753
No. of parameters	225
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.33

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), CAD-4 Software (Enraf–Nonius, 1989, XCAD (McArdle, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEX (McArdle, 1995).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O—H1O···N5ⁱ	0.78 (4)	2.04 (4)	2.787 (3)	159 (3)
N3—H3N···Oⁱⁱ	0.83 (3)	2.09 (2)	2.889 (3)	163 (2)

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

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