In the title compound, [ZnCl
2(C
8H
6N
2)
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.
Supporting information
CCDC reference: 219854
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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.
Crystal data top
[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) Å3 | 0.4 × 0.3 × 0.2 mm |
Z = 4 | |
Data collection top
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 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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0725P)2 + 2.0204P] where P = (Fo2 + 2Fc2)/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 top
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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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···Cl1i | 0.93 | 2.78 | 3.637 (5) | 153 |
Symmetry code: (i) −x+1, −y+2, −z+1. |