Di­chloro­bis­(phthalazine)­zinc(II)

In the title compound, [ZnCl₂(C₈H₆N₂)₂], the Zn^II atom is coordinated in a distorted tetrahedral environment by two Cl atoms and two N atoms from the phthalazine ligands. There is an intramolecular C—H...N interaction between the phthal­azine ligands.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.040
• wR factor = 0.100
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Zn     -   Cl2     ..      11.07 su

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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

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Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1993); cell refinement: SHELXL97 (Sheldrick, 1997); data reduction: CAD-4 EXPRESS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

(I)

Crystal data

[ZnCl2(C8H6N2)2]	F(000) = 800
Mr = 396.6	Dx = 1.638 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 7.499 (1) Å	θ = 2.8–26.3°
b = 14.525 (2) Å	µ = 1.86 mm^−1
c = 15.049 (1) Å	T = 293 K
β = 101.15 (4)°	Prism, colourless
V = 1608.1 (4) Å^3	0.4 × 0.3 × 0.2 mm
Z = 4

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.04
ω/2θ scans	θmax = 26.3°, θmin = 2.8°
Absorption correction: ψ scan (North et al., 1968)	h = −9→9
Tmin = 0.503, Tmax = 0.688	k = 0→18
3384 measured reflections	l = 0→18
3258 independent reflections	3 standard reflections every 120 min
1895 reflections with I > 2σ(I)	intensity decay: 0.1%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.100	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0725P)^2 + 2.0204P] where P = (Fo^2 + 2Fc^2)/3
3258 reflections	(Δ/σ)max = 0.001
212 parameters	Δρmax = 0.42 e Å^−3
0 restraints	Δρmin = −0.41 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.58338 (15)	0.77309 (7)	0.54595 (7)	0.0457 (3)
Cl2	0.08715 (16)	0.71804 (7)	0.47488 (8)	0.0529 (3)
Zn	0.30597 (7)	0.82282 (3)	0.48396 (3)	0.03745 (16)
N1	0.3229 (4)	0.8843 (2)	0.3641 (2)	0.0356 (8)
N2	0.3495 (5)	0.8194 (2)	0.3015 (2)	0.0437 (9)
N3	0.2358 (5)	0.9214 (2)	0.5702 (2)	0.0386 (8)
N4	0.2329 (5)	1.0109 (2)	0.5412 (2)	0.0443 (9)
C1	0.3696 (6)	0.8495 (3)	0.2222 (3)	0.0422 (11)
C2	0.3627 (5)	0.9435 (3)	0.1951 (3)	0.0336 (9)
C3	0.3760 (6)	0.9733 (3)	0.1077 (3)	0.0467 (11)
C4	0.3682 (6)	1.0649 (3)	0.0888 (3)	0.0481 (12)
C5	0.3497 (6)	1.1291 (3)	0.1551 (3)	0.0443 (11)
C6	0.3351 (6)	1.1028 (3)	0.2401 (3)	0.0413 (11)
C7	0.3396 (5)	1.0076 (3)	0.2607 (2)	0.0320 (9)
C8	0.3209 (5)	0.9724 (3)	0.3458 (2)	0.0353 (10)
C9	0.1975 (6)	1.0747 (3)	0.5966 (3)	0.0420 (11)
C10	0.1625 (5)	1.0596 (3)	0.6844 (3)	0.0372 (10)
C11	0.1276 (6)	1.1294 (3)	0.7432 (3)	0.0481 (12)
C12	0.1025 (6)	1.1060 (4)	0.8275 (3)	0.0574 (14)
C13	0.1072 (6)	1.0145 (4)	0.8556 (3)	0.0563 (13)
C14	0.1396 (6)	0.9453 (3)	0.8006 (3)	0.0503 (12)
C15	0.1676 (5)	0.9679 (3)	0.7133 (3)	0.0378 (10)
C16	0.2048 (5)	0.9015 (3)	0.6505 (3)	0.0412 (11)
H1	0.3901	0.8059	0.18	0.051
H2	0.3899	0.9309	0.0633	0.056
H3	0.3752	1.0849	0.0309	0.058
H4	0.3474	1.1915	0.1409	0.053
H5	0.3223	1.1464	0.2838	0.05
H6	0.3066	1.0138	0.3911	0.042
H7	0.1951	1.1353	0.5765	0.05
H8	0.1218	1.1907	0.7249	0.058
H9	0.0816	1.1521	0.8672	0.069
H10	0.0877	1.0007	0.9134	0.068
H11	0.1433	0.8844	0.8199	0.06
H12	0.2073	0.8399	0.6675	0.049

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn	0.0522 (3)	0.0284 (2)	0.0342 (3)	0.0020 (2)	0.0144 (2)	0.0040 (2)
Cl1	0.0549 (7)	0.0445 (6)	0.0377 (6)	0.0013 (5)	0.0093 (5)	0.0097 (5)
Cl2	0.0628 (8)	0.0409 (6)	0.0581 (7)	−0.0029 (6)	0.0194 (6)	−0.0092 (6)
N2	0.059 (2)	0.0310 (18)	0.046 (2)	−0.0013 (18)	0.0211 (18)	0.0069 (18)
N3	0.047 (2)	0.0303 (18)	0.040 (2)	−0.0001 (16)	0.0136 (17)	0.0049 (16)
N4	0.065 (3)	0.0324 (19)	0.040 (2)	0.0000 (16)	0.0221 (19)	0.0019 (18)
N1	0.042 (2)	0.0318 (19)	0.0335 (18)	0.0044 (16)	0.0090 (16)	0.0036 (16)
C9	0.050 (3)	0.026 (2)	0.053 (3)	0.001 (2)	0.018 (2)	0.002 (2)
C2	0.034 (2)	0.035 (2)	0.032 (2)	−0.0017 (19)	0.0078 (19)	−0.0060 (19)
C10	0.033 (2)	0.040 (2)	0.041 (2)	−0.003 (2)	0.011 (2)	−0.0014 (19)
C16	0.049 (3)	0.031 (2)	0.046 (3)	0.009 (2)	0.015 (2)	0.005 (2)
C6	0.050 (3)	0.034 (2)	0.039 (2)	−0.005 (2)	0.006 (2)	−0.001 (2)
C11	0.048 (3)	0.044 (3)	0.055 (3)	−0.014 (2)	0.018 (2)	−0.004 (2)
C8	0.041 (3)	0.035 (2)	0.028 (2)	−0.0027 (19)	0.0037 (19)	0.0048 (19)
C14	0.056 (3)	0.060 (3)	0.036 (2)	0.009 (2)	0.012 (2)	0.000 (3)
C3	0.059 (3)	0.050 (3)	0.035 (2)	−0.004 (2)	0.017 (2)	−0.009 (2)
C7	0.032 (2)	0.032 (2)	0.032 (2)	−0.0013 (18)	0.0042 (18)	−0.0042 (18)
C1	0.056 (3)	0.031 (2)	0.043 (3)	−0.008 (2)	0.019 (2)	0.000 (2)
C15	0.033 (2)	0.043 (2)	0.038 (2)	−0.001 (2)	0.008 (2)	0.003 (2)
C12	0.050 (3)	0.076 (4)	0.047 (3)	−0.031 (3)	0.011 (2)	−0.006 (3)
C5	0.059 (3)	0.033 (2)	0.040 (2)	0.009 (2)	0.007 (2)	−0.003 (2)
C13	0.051 (3)	0.085 (4)	0.035 (3)	−0.008 (3)	0.014 (2)	−0.006 (3)
C4	0.063 (3)	0.048 (3)	0.035 (2)	0.011 (2)	0.014 (2)	−0.011 (2)

Geometric parameters (Å, º)

Zn—N1	2.038 (3)	C6—C5	1.361 (5)
Zn—N3	2.068 (3)	C6—C7	1.417 (5)
Zn—Cl2	2.223 (1)	C6—H5	0.9300
Zn—Cl1	2.229 (1	C11—C12	1.361 (6)
N2—C1	1.307 (5)	C11—H8	0.9300
N2—N1	1.374 (4)	C8—C7	1.411 (5)
N3—C16	1.307 (5)	C8—H6	0.9300
N3—N4	1.370 (4)	C14—C13	1.355 (6)
N4—C9	1.308 (5)	C14—C15	1.409 (5)
N1—C8	1.309 (4)	C14—H11	0.9300
C9—C10	1.413 (5)	C3—C4	1.359 (5)
C9—H7	0.9300	C3—H2	0.9300
C2—C7	1.392 (5)	C1—H1	0.9300
C2—C3	1.407 (5)	C12—C13	1.393 (6)
C2—C1	1.424 (5)	C12—H9	0.9300
C10—C15	1.399 (5)	C5—C4	1.391 (5)
C10—C11	1.404 (5)	C5—H4	0.9300
C16—C15	1.414 (5)	C13—H10	0.9300
C16—H12	0.9300	C4—H3	0.9300
N1—Zn—N3	108.58 (13)	C10—C11—H8	120.6
N1—Zn—Cl2	114.65 (10)	N1—C8—C7	123.1 (4)
N3—Zn—Cl2	103.80 (10)	N1—C8—H6	118.4
N1—Zn—Cl1	107.43 (10)	C7—C8—H6	118.4
N3—Zn—Cl1	106.98 (10)	C13—C14—C15	118.3 (4)
Cl2—Zn—Cl1	114.96 (5)	C13—C14—H11	120.8
C1—N2—N1	117.0 (3)	C15—C14—H11	120.8
C16—N3—N4	120.7 (3)	C4—C3—C2	119.2 (4)
C16—N3—Zn	122.7 (3)	C4—C3—H2	120.4
N4—N3—Zn	116.6 (2)	C2—C3—H2	120.4
C9—N4—N3	117.5 (3)	C2—C7—C8	116.7 (3)
C8—N1—N2	121.6 (3)	C2—C7—C6	119.9 (3)
C8—N1—Zn	127.9 (3)	C8—C7—C6	123.3 (4)
N2—N1—Zn	110.4 (2)	N2—C1—C2	125.3 (4)
N4—C9—C10	125.8 (4)	N2—C1—H1	117.3
N4—C9—H7	117.1	C2—C1—H1	117.3
C10—C9—H7	117.1	C10—C15—C14	120.7 (4)
C7—C2—C3	119.9 (4)	C10—C15—C16	116.0 (4)
C7—C2—C1	116.2 (3)	C14—C15—C16	123.2 (4)
C3—C2—C1	123.9 (4)	C11—C12—C13	121.5 (4)
C15—C10—C11	119.3 (4)	C11—C12—H9	119.3
C15—C10—C9	116.0 (4)	C13—C12—H9	119.3
C11—C10—C9	124.6 (4)	C6—C5—C4	121.5 (4)
N3—C16—C15	124.1 (4)	C6—C5—H4	119.2
N3—C16—H12	118	C4—C5—H4	119.2
C15—C16—H12	118	C14—C13—C12	121.3 (4)
C5—C6—C7	118.5 (4)	C14—C13—H10	119.4
C5—C6—H5	120.8	C12—C13—H10	119.4
C7—C6—H5	120.8	C3—C4—C5	120.9 (4)
C12—C11—C10	118.9 (4)	C3—C4—H3	119.6
C12—C11—H8	120.6	C5—C4—H3	119.6
N1—Zn—N3—C16	176.0 (3)	C1—C2—C3—C4	−179.9 (4)
Cl2—Zn—N3—C16	53.6 (3)	C3—C2—C7—C8	177.8 (4)
Cl1—Zn—N3—C16	−68.3 (3)	C1—C2—C7—C8	−1.5 (5)
N1—Zn—N3—N4	−7.5 (3)	C3—C2—C7—C6	−2.0 (6)
Cl2—Zn—N3—N4	−129.9 (3)	C1—C2—C7—C6	178.7 (4)
Cl1—Zn—N3—N4	108.1 (3)	N1—C8—C7—C2	−0.7 (6)
C16—N3—N4—C9	−0.2 (6)	N1—C8—C7—C6	179.1 (4)
Zn—N3—N4—C9	−176.8 (3)	C5—C6—C7—C2	1.4 (6)
C1—N2—N1—C8	−1.2 (6)	C5—C6—C7—C8	−178.3 (4)
C1—N2—N1—Zn	−177.5 (3)	N1—N2—C1—C2	−1.3 (7)
N3—Zn—N1—C8	10.6 (4)	C7—C2—C1—N2	2.6 (7)
Cl2—Zn—N1—C8	126.1 (3)	C3—C2—C1—N2	−176.7 (4)
Cl1—Zn—N1—C8	−104.8 (3)	C11—C10—C15—C14	−0.5 (6)
N3—Zn—N1—N2	−173.4 (2)	C9—C10—C15—C14	178.3 (4)
Cl2—Zn—N1—N2	−57.8 (3)	C11—C10—C15—C16	−179.6 (4)
Cl1—Zn—N1—N2	71.3 (3)	C9—C10—C15—C16	−0.8 (6)
N3—N4—C9—C10	0.3 (6)	C13—C14—C15—C10	0.2 (7)
N4—C9—C10—C15	0.3 (6)	C13—C14—C15—C16	179.2 (4)
N4—C9—C10—C11	179.0 (4)	N3—C16—C15—C10	0.9 (6)
N4—N3—C16—C15	−0.4 (6)	N3—C16—C15—C14	−178.1 (4)
Zn—N3—C16—C15	175.9 (3)	C10—C11—C12—C13	−1.2 (7)
C15—C10—C11—C12	1.0 (7)	C7—C6—C5—C4	0.2 (7)
C9—C10—C11—C12	−177.6 (4)	C15—C14—C13—C12	−0.4 (7)
N2—N1—C8—C7	2.2 (6)	C11—C12—C13—C14	0.9 (8)
Zn—N1—C8—C7	177.8 (3)	C2—C3—C4—C5	0.9 (7)
C7—C2—C3—C4	0.8 (6)	C6—C5—C4—C3	−1.4 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H6···N4	0.93	2.43	3.185 (5)	139
C6—H5···Cl1^i	0.93	2.78	3.637 (5)	153

Symmetry code: (i) −x+1, −y+2, −z+1.