[N,N-Bis(2-pyridylmeth­yl)glycinato-κ4N,N′,N′′,O]dichloridoiron(III)–[N,N-bis­(2-pyridylmeth­yl)glycine-κ4N,N′,N′′,O]dichloridozinc(II) (1/1)

Nielsen, A.; McKenzie, C.J.; Bond, A.D.

doi:10.1107/S1600536809051022

metal-organic compounds

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Volume 65| Part 12| December 2009| Page m1706

doi:10.1107/S1600536809051022

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[N,N-Bis(2-pyridylmethyl)glycinato-κ⁴N,N′,N′′,O]dichloridoiron(III)–[N,N-bis(2-pyridylmethyl)glycine-κ⁴N,N′,N′′,O]dichloridozinc(II) (1/1)

Anne Nielsen,^a Christine J. McKenzie ^a and Andrew D. Bond ^a ^*

^aUniversity of Southern Denmark, Department of Physics and Chemistry, Campusvej 55, 5230 Odense M, Denmark
^*Correspondence e-mail: adb@chem.sdu.dk

(Received 25 November 2009; accepted 26 November 2009; online 28 November 2009)

The title compound, [Fe(C₁₄H₁₄N₃O₂)Cl₂]·[ZnCl₂(C₁₄H₁₅N₃O₂)], is formulated as [Fe^III(bpg)Cl₂][Zn^IICl₂(bpgH)], where bpg is the tetradentate ligand N,N-bis(2-pyridylmethyl)glycine. The structure contains one crystallographically distinct complex with Fe^III and Zn^II atoms present in a 50:50 ratio in a single-atom site. The non-coordinated O atoms of the carboxyl groups of bpg meet across crystallographic inversion centres, forming O—H⋯O hydrogen bonds that include only one H atom per two complexes, consistent with the 1:1 disorder of Fe^III and Zn^II.

Related literature

For related Fe^III structures of bpg, see: Mortensen et al. (2004 ). For details of the synthesis, see: Suzuki et al. (1988 ).

Experimental

Crystal data

[Fe(C₁₄H₁₄N₃O₂)Cl₂]·[ZnCl₂(C₁₄H₁₅N₃O₂)]
M_r = 776.59
Monoclinic, P 2₁ /c
a = 8.8710 (3) Å
b = 13.1898 (5) Å
c = 13.3983 (4) Å
β = 91.737 (2)°
V = 1566.97 (9) Å³
Z = 2
Mo Kα radiation
μ = 1.62 mm⁻¹
T = 180 K
0.20 × 0.20 × 0.15 mm

Data collection

Bruker–Nonius X8APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.701, T_max = 0.794
32580 measured reflections
4775 independent reflections
4248 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.132
S = 1.36
4775 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.71 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O2ⁱ	0.93	1.64	2.559 (6)	169
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2003 ); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809051022/jh2118sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809051022/jh2118Isup2.hkl

checkCIF report

Comment top

Crystallization of the title compound, [FeCl₂(bpg)][ZnCl₂(bpgH)] (where bpg denotes the tetradentate ligand N,N-bis(2-pyridylmethyl)glycine), was surprising given the presence of water in its preparation. In our hands, simple binary mixtures of bpgH and FeCl₃ in water-containing solutions do not yield the complex [FeCl₂(bpg)]. If only chloride ions but not Zn^II are present in equivalent reaction mixtures (i.e. aerobic conditions and containing water), oligomeric (hydr)oxo-bridged Fe^III complexes are formed, such as [Fe₂(O)(bpg)₂(H₂O)₂](ClO₄)₂ and [Fe₃(O)₂(OH)(bpg)₃](ClO₄) (Mortensen et al., 2004). Addition of Zn^II has in this case enabled isolation of [FeCl₂(bpg)] from water as one component of the co-crystal.

Related literature top

For related Fe^III structures of bpg, see: Mortensen et al. (2004). For details of the synthesis, see: Suzuki et al. (1988).

Experimental top

N,N-Bis(2-pyridylmethyl)glycine (bpgH) was prepared according to a literature method (Suzuki et al., 1988). BpgH (125 mg, 49 mmol) was then dissolved in hot acetonitrile (5 ml) and water (0.5 ml), before Fe(NO₃)₃.9H₂O (99 mg, 24 mmol), ZnCl₂ (67 mg, 49 mmol) and NH₄Cl (78 mg, 15 mmol) were added. A few yellow crystals of the title compound were deposited overnight.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure with displacement ellipsoids shown at 50% probability for non-H atoms.
	Fig. 2. Projection along the a axis showing hydrogen bonds (dashed lines) formed between bpg(H) ligands across crystallographic inversion centres.

[N,N-Bis(2-pyridylmethyl)glycinato- κ⁴N,N',N'',O]dichloridoiron(III)– [N,N-bis(2-pyridylmethyl)glycine- κ⁴N,N',N'',O]dichloridozinc(II) (1/1) top

Crystal data top

[Fe(C₁₄H₁₄N₃O₂)Cl₂]·[ZnCl₂(C₁₄H₁₅N₃O₂)]	F(000) = 790
M_r = 776.59	D_x = 1.646 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5945 reflections
a = 8.8710 (3) Å	θ = 2.3–29.9°
b = 13.1898 (5) Å	µ = 1.62 mm⁻¹
c = 13.3983 (4) Å	T = 180 K
β = 91.737 (2)°	Block, yellow
V = 1566.97 (9) Å³	0.20 × 0.20 × 0.15 mm
Z = 2

Data collection top

Bruker–Nonius X8APEXII CCD diffractometer	4775 independent reflections
Radiation source: fine-focus sealed tube	4248 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Thin–slice ω and ϕ scans	θ_max = 30.5°, θ_min = 3.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −12→12
T_min = 0.701, T_max = 0.794	k = −18→18
32580 measured reflections	l = −19→18

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H-atom parameters constrained
S = 1.36	w = 1/[σ²(F_o²) + 7.0062P] where P = (F_o² + 2F_c²)/3
4775 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.71 e Å⁻³

Crystal data top

[Fe(C₁₄H₁₄N₃O₂)Cl₂]·[ZnCl₂(C₁₄H₁₅N₃O₂)]	V = 1566.97 (9) Å³
M_r = 776.59	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.8710 (3) Å	µ = 1.62 mm⁻¹
b = 13.1898 (5) Å	T = 180 K
c = 13.3983 (4) Å	0.20 × 0.20 × 0.15 mm
β = 91.737 (2)°

Data collection top

Bruker–Nonius X8APEXII CCD diffractometer	4775 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	4248 reflections with I > 2σ(I)
T_min = 0.701, T_max = 0.794	R_int = 0.031
32580 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 1.36	Δρ_max = 0.55 e Å⁻³
4775 reflections	Δρ_min = −0.71 e Å⁻³
199 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	Occ. (<1)
Fe1	0.30263 (5)	0.42993 (3)	0.31348 (3)	0.01709 (11)	0.50
Zn1	0.30263 (5)	0.42993 (3)	0.31348 (3)	0.01709 (11)	0.50
Cl1	0.19027 (10)	0.35846 (7)	0.45311 (7)	0.02319 (19)
Cl2	0.30370 (13)	0.59544 (7)	0.35454 (8)	0.0290 (2)
O1	0.3982 (4)	0.4689 (2)	0.1686 (2)	0.0295 (6)
O2	0.4679 (4)	0.4082 (2)	0.0219 (2)	0.0326 (7)
H2	0.4790	0.4759	0.0050	0.049*	0.50
N1	0.5237 (4)	0.3803 (2)	0.3539 (2)	0.0204 (6)
N2	0.3235 (3)	0.2778 (2)	0.2375 (2)	0.0171 (6)
N3	0.0989 (4)	0.4170 (3)	0.2225 (2)	0.0215 (6)
C1	0.6376 (4)	0.4414 (3)	0.3838 (3)	0.0245 (8)
H1A	0.6184	0.5117	0.3927	0.029*
C2	0.7825 (5)	0.4048 (4)	0.4022 (3)	0.0291 (9)
H2A	0.8617	0.4493	0.4228	0.035*
C3	0.8095 (5)	0.3026 (4)	0.3899 (3)	0.0320 (10)
H3A	0.9081	0.2759	0.4010	0.038*
C4	0.6917 (5)	0.2392 (3)	0.3615 (3)	0.0280 (8)
H4A	0.7076	0.1684	0.3548	0.034*
C5	0.5506 (4)	0.2805 (3)	0.3429 (3)	0.0208 (7)
C6	0.4167 (4)	0.2175 (3)	0.3096 (3)	0.0202 (7)
H6A	0.4512	0.1543	0.2775	0.024*
H6B	0.3564	0.1989	0.3678	0.024*
C7	0.1677 (4)	0.2401 (3)	0.2253 (3)	0.0215 (7)
H7A	0.1323	0.2150	0.2901	0.026*
H7B	0.1647	0.1829	0.1774	0.026*
C8	0.0656 (4)	0.3237 (3)	0.1875 (3)	0.0230 (7)
C9	−0.0583 (5)	0.3063 (4)	0.1241 (3)	0.0340 (10)
H9A	−0.0797	0.2399	0.1001	0.041*
C10	−0.1499 (6)	0.3865 (5)	0.0964 (4)	0.0445 (13)
H10A	−0.2355	0.3759	0.0534	0.053*
C11	−0.1162 (6)	0.4821 (4)	0.1318 (4)	0.0465 (14)
H11A	−0.1784	0.5382	0.1137	0.056*
C12	0.0097 (5)	0.4952 (4)	0.1942 (4)	0.0336 (10)
H12A	0.0338	0.5613	0.2178	0.040*
C13	0.3965 (4)	0.2893 (3)	0.1407 (3)	0.0198 (7)
H13A	0.3337	0.2553	0.0883	0.024*
H13B	0.4956	0.2548	0.1442	0.024*
C14	0.4195 (4)	0.3982 (3)	0.1113 (3)	0.0190 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0191 (2)	0.0150 (2)	0.0172 (2)	−0.00111 (17)	0.00049 (15)	0.00011 (17)
Zn1	0.0191 (2)	0.0150 (2)	0.0172 (2)	−0.00111 (17)	0.00049 (15)	0.00011 (17)
Cl1	0.0217 (4)	0.0273 (5)	0.0207 (4)	−0.0020 (3)	0.0013 (3)	0.0032 (3)
Cl2	0.0400 (6)	0.0201 (4)	0.0272 (5)	0.0007 (4)	0.0063 (4)	−0.0067 (4)
O1	0.0351 (16)	0.0169 (13)	0.0363 (17)	0.0000 (12)	0.0006 (13)	−0.0069 (12)
O2	0.0476 (19)	0.0233 (15)	0.0271 (15)	−0.0051 (13)	0.0057 (13)	0.0043 (12)
N1	0.0204 (15)	0.0210 (15)	0.0196 (14)	−0.0020 (12)	−0.0012 (11)	−0.0008 (12)
N2	0.0173 (14)	0.0162 (14)	0.0178 (13)	−0.0016 (11)	−0.0002 (11)	0.0006 (11)
N3	0.0205 (15)	0.0223 (16)	0.0216 (15)	0.0013 (12)	−0.0015 (12)	−0.0004 (12)
C1	0.0231 (18)	0.0261 (19)	0.0243 (18)	−0.0055 (15)	0.0003 (14)	−0.0037 (15)
C2	0.0209 (18)	0.041 (2)	0.0253 (19)	−0.0060 (17)	−0.0018 (15)	−0.0064 (17)
C3	0.0211 (19)	0.047 (3)	0.028 (2)	0.0080 (18)	−0.0049 (15)	−0.0064 (19)
C4	0.026 (2)	0.031 (2)	0.0268 (19)	0.0081 (16)	−0.0041 (15)	−0.0039 (16)
C5	0.0213 (17)	0.0243 (18)	0.0166 (15)	0.0013 (14)	−0.0013 (13)	−0.0016 (13)
C6	0.0226 (17)	0.0161 (16)	0.0218 (17)	0.0015 (13)	−0.0010 (13)	0.0005 (13)
C7	0.0208 (17)	0.0186 (17)	0.0249 (17)	−0.0041 (14)	−0.0034 (13)	−0.0010 (14)
C8	0.0193 (17)	0.0273 (19)	0.0223 (17)	−0.0033 (15)	−0.0014 (13)	−0.0025 (15)
C9	0.027 (2)	0.040 (3)	0.034 (2)	−0.0024 (18)	−0.0101 (17)	−0.0074 (19)
C10	0.030 (2)	0.057 (3)	0.045 (3)	0.010 (2)	−0.018 (2)	−0.011 (2)
C11	0.036 (3)	0.051 (3)	0.052 (3)	0.022 (2)	−0.020 (2)	−0.011 (2)
C12	0.031 (2)	0.029 (2)	0.041 (3)	0.0087 (18)	−0.0066 (18)	−0.0021 (19)
C13	0.0267 (18)	0.0161 (16)	0.0168 (15)	0.0002 (13)	0.0028 (13)	0.0007 (12)
C14	0.0204 (16)	0.0185 (16)	0.0179 (16)	0.0000 (13)	−0.0005 (13)	−0.0019 (13)

Geometric parameters (Å, º) top

Fe1—N1	2.122 (3)	C3—H3A	0.950
Fe1—N3	2.156 (3)	C4—C5	1.381 (5)
Fe1—O1	2.202 (3)	C4—H4A	0.950
Fe1—Cl2	2.2512 (11)	C5—C6	1.506 (5)
Fe1—N2	2.260 (3)	C6—H6A	0.990
Fe1—Cl1	2.3441 (10)	C6—H6B	0.990
O1—C14	1.226 (5)	C7—C8	1.505 (5)
O2—C14	1.291 (5)	C7—H7A	0.990
O2—H2	0.927	C7—H7B	0.990
N1—C1	1.345 (5)	C8—C9	1.387 (5)
N1—C5	1.346 (5)	C9—C10	1.378 (7)
N2—C7	1.473 (5)	C9—H9A	0.950
N2—C13	1.475 (5)	C10—C11	1.377 (8)
N2—C6	1.483 (5)	C10—H10A	0.950
N3—C8	1.347 (5)	C11—C12	1.386 (6)
N3—C12	1.348 (5)	C11—H11A	0.950
C1—C2	1.388 (6)	C12—H12A	0.950
C1—H1A	0.950	C13—C14	1.504 (5)
C2—C3	1.381 (7)	C13—H13A	0.990
C2—H2A	0.950	C13—H13B	0.990
C3—C4	1.382 (6)

N1—Fe1—N3	150.70 (12)	C3—C4—H4A	120.5
N1—Fe1—O1	85.37 (12)	N1—C5—C4	121.9 (4)
N3—Fe1—O1	81.87 (12)	N1—C5—C6	115.5 (3)
N1—Fe1—Cl2	103.88 (9)	C4—C5—C6	122.6 (4)
N3—Fe1—Cl2	102.26 (9)	N2—C6—C5	108.4 (3)
O1—Fe1—Cl2	89.45 (8)	N2—C6—H6A	110.0
N1—Fe1—N2	75.71 (11)	C5—C6—H6A	110.0
N3—Fe1—N2	75.74 (12)	N2—C6—H6B	110.0
O1—Fe1—N2	76.77 (11)	C5—C6—H6B	110.0
Cl2—Fe1—N2	166.22 (8)	H6A—C6—H6B	108.4
N1—Fe1—Cl1	94.84 (9)	N2—C7—C8	110.1 (3)
N3—Fe1—Cl1	92.86 (9)	N2—C7—H7A	109.6
O1—Fe1—Cl1	168.98 (8)	C8—C7—H7A	109.6
Cl2—Fe1—Cl1	101.17 (4)	N2—C7—H7B	109.6
N2—Fe1—Cl1	92.57 (8)	C8—C7—H7B	109.6
C14—O1—Fe1	116.5 (3)	H7A—C7—H7B	108.2
C14—O2—H2	111.5	N3—C8—C9	121.7 (4)
C1—N1—C5	119.0 (3)	N3—C8—C7	115.4 (3)
C1—N1—Fe1	124.9 (3)	C9—C8—C7	122.8 (4)
C5—N1—Fe1	116.1 (2)	C10—C9—C8	119.2 (4)
C7—N2—C13	111.8 (3)	C10—C9—H9A	120.4
C7—N2—C6	113.2 (3)	C8—C9—H9A	120.4
C13—N2—C6	112.1 (3)	C11—C10—C9	119.4 (4)
C7—N2—Fe1	105.1 (2)	C11—C10—H10A	120.3
C13—N2—Fe1	110.4 (2)	C9—C10—H10A	120.3
C6—N2—Fe1	103.6 (2)	C10—C11—C12	119.0 (5)
C8—N3—C12	118.7 (4)	C10—C11—H11A	120.5
C8—N3—Fe1	116.2 (3)	C12—C11—H11A	120.5
C12—N3—Fe1	125.0 (3)	N3—C12—C11	122.0 (5)
N1—C1—C2	121.9 (4)	N3—C12—H12A	119.0
N1—C1—H1A	119.1	C11—C12—H12A	119.0
C2—C1—H1A	119.1	N2—C13—C14	113.3 (3)
C3—C2—C1	118.8 (4)	N2—C13—H13A	108.9
C3—C2—H2A	120.6	C14—C13—H13A	108.9
C1—C2—H2A	120.6	N2—C13—H13B	108.9
C2—C3—C4	119.4 (4)	C14—C13—H13B	108.9
C2—C3—H3A	120.3	H13A—C13—H13B	107.7
C4—C3—H3A	120.3	O1—C14—O2	124.4 (4)
C5—C4—C3	119.0 (4)	O1—C14—C13	122.5 (3)
C5—C4—H4A	120.5	O2—C14—C13	113.1 (3)

N1—Fe1—O1—C14	77.2 (3)	C5—N1—C1—C2	1.1 (6)
N3—Fe1—O1—C14	−76.3 (3)	Fe1—N1—C1—C2	−175.2 (3)
Cl2—Fe1—O1—C14	−178.8 (3)	N1—C1—C2—C3	−0.5 (6)
N2—Fe1—O1—C14	0.8 (3)	C1—C2—C3—C4	−1.0 (7)
Cl1—Fe1—O1—C14	−14.3 (7)	C2—C3—C4—C5	2.0 (6)
N3—Fe1—N1—C1	144.7 (3)	C1—N1—C5—C4	−0.1 (6)
O1—Fe1—N1—C1	80.4 (3)	Fe1—N1—C5—C4	176.5 (3)
Cl2—Fe1—N1—C1	−7.9 (3)	C1—N1—C5—C6	179.8 (3)
N2—Fe1—N1—C1	157.9 (3)	Fe1—N1—C5—C6	−3.7 (4)
Cl1—Fe1—N1—C1	−110.7 (3)	C3—C4—C5—N1	−1.5 (6)
N3—Fe1—N1—C5	−31.7 (4)	C3—C4—C5—C6	178.7 (4)
O1—Fe1—N1—C5	−96.0 (3)	C7—N2—C6—C5	−160.8 (3)
Cl2—Fe1—N1—C5	175.7 (3)	C13—N2—C6—C5	71.5 (4)
N2—Fe1—N1—C5	−18.5 (3)	Fe1—N2—C6—C5	−47.5 (3)
Cl1—Fe1—N1—C5	73.0 (3)	N1—C5—C6—N2	36.7 (4)
N1—Fe1—N2—C7	154.6 (2)	C4—C5—C6—N2	−143.5 (4)
N3—Fe1—N2—C7	−32.0 (2)	C13—N2—C7—C8	−75.2 (4)
O1—Fe1—N2—C7	−116.9 (2)	C6—N2—C7—C8	157.0 (3)
Cl2—Fe1—N2—C7	−115.3 (4)	Fe1—N2—C7—C8	44.6 (3)
Cl1—Fe1—N2—C7	60.3 (2)	C12—N3—C8—C9	−0.5 (6)
N1—Fe1—N2—C13	−84.6 (2)	Fe1—N3—C8—C9	−176.8 (3)
N3—Fe1—N2—C13	88.7 (2)	C12—N3—C8—C7	−178.1 (4)
O1—Fe1—N2—C13	3.9 (2)	Fe1—N3—C8—C7	5.6 (4)
Cl2—Fe1—N2—C13	5.4 (5)	N2—C7—C8—N3	−35.6 (5)
Cl1—Fe1—N2—C13	−179.0 (2)	N2—C7—C8—C9	146.9 (4)
N1—Fe1—N2—C6	35.6 (2)	N3—C8—C9—C10	−0.2 (7)
N3—Fe1—N2—C6	−151.1 (2)	C7—C8—C9—C10	177.2 (4)
O1—Fe1—N2—C6	124.1 (2)	C8—C9—C10—C11	0.3 (8)
Cl2—Fe1—N2—C6	125.6 (3)	C9—C10—C11—C12	0.2 (9)
Cl1—Fe1—N2—C6	−58.8 (2)	C8—N3—C12—C11	1.1 (7)
N1—Fe1—N3—C8	28.4 (4)	Fe1—N3—C12—C11	177.0 (4)
O1—Fe1—N3—C8	93.5 (3)	C10—C11—C12—N3	−1.0 (9)
Cl2—Fe1—N3—C8	−178.8 (3)	C7—N2—C13—C14	109.1 (3)
N2—Fe1—N3—C8	15.2 (3)	C6—N2—C13—C14	−122.4 (3)
Cl1—Fe1—N3—C8	−76.7 (3)	Fe1—N2—C13—C14	−7.5 (4)
N1—Fe1—N3—C12	−147.6 (3)	Fe1—O1—C14—O2	176.6 (3)
O1—Fe1—N3—C12	−82.5 (4)	Fe1—O1—C14—C13	−5.8 (5)
Cl2—Fe1—N3—C12	5.2 (4)	N2—C13—C14—O1	9.3 (5)
N2—Fe1—N3—C12	−160.8 (4)	N2—C13—C14—O2	−172.8 (3)
Cl1—Fe1—N3—C12	107.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O2ⁱ	0.93	1.64	2.559 (6)	169

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[Fe(C₁₄H₁₄N₃O₂)Cl₂]·[ZnCl₂(C₁₄H₁₅N₃O₂)]
M_r	776.59
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	180
a, b, c (Å)	8.8710 (3), 13.1898 (5), 13.3983 (4)
β (°)	91.737 (2)
V (Å³)	1566.97 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.62
Crystal size (mm)	0.20 × 0.20 × 0.15

Data collection
Diffractometer	Bruker–Nonius X8APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.701, 0.794
No. of measured, independent and observed [I > 2σ(I)] reflections	32580, 4775, 4248
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.714

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.132, 1.36
No. of reflections	4775
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.71

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2003), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O2ⁱ	0.93	1.64	2.559 (6)	169.4

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

We are grateful to the Danish Natural Sciences Research Council and the Carlsberg Foundation for provision of the X-ray equipment.

References

Bruker (2003). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Mortensen, M. N., Jensen, B., Hazell, A., Bond, A. D. & McKenzie, C. J. (2004). Dalton Trans. pp. 3396–3402. Web of Science CSD CrossRef Google Scholar
Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef IUCr Journals Google Scholar
Suzuki, M., Senda, H., Kobayashi, Y., Oshio, H. & Uehara, A. (1988). Chem. Lett. pp. 1763–1766. CrossRef Web of Science Google Scholar

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