In the title compound, [Zn(C14H8Br2N2O3)(C5H5N)2], the ZnII ion is coordinated by one N and two O atoms from a Schiff base ligand and by the N atoms of two pyridine molecules to form a distorted trigonal–bipyramidal geometry.
Supporting information
CCDC reference: 601786
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.012 Å
- R factor = 0.052
- wR factor = 0.157
- Data-to-parameter ratio = 15.4
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for C16 - C17 .. 9.47 su
PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C16
Alert level C
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C23
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 12
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
2 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
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
[3,5-Dibromosalicylaldehyde
(2-hydroxybenzoyl)hydrazonato-
κ3O,
N,
O']bis(pyridine-
κN)zinc(II)
top
Crystal data top
[Zn(C14H8Br2N2O3)(C5H5N)2] | Z = 2 |
Mr = 635.61 | F(000) = 628 |
Triclinic, P1 | Dx = 1.712 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.9000 (11) Å | Cell parameters from 1568 reflections |
b = 12.2172 (14) Å | θ = 2.5–21.0° |
c = 13.1342 (16) Å | µ = 4.27 mm−1 |
α = 101.696 (2)° | T = 292 K |
β = 103.519 (2)° | Block, green |
γ = 110.744 (2)° | 0.20 × 0.20 × 0.20 mm |
V = 1232.9 (3) Å3 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2763 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.021 |
Graphite monochromator | θmax = 26.0°, θmin = 1.7° |
φ and ω scans | h = −10→9 |
6745 measured reflections | k = −12→15 |
4740 independent reflections | l = −15→16 |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.157 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0716P)2 + 0.5653P] where P = (Fo2 + 2Fc2)/3 |
4740 reflections | (Δ/σ)max = 0.001 |
308 parameters | Δρmax = 0.62 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
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 | Uiso*/Ueq | |
Zn1 | 0.90729 (9) | 0.80295 (6) | 0.09455 (6) | 0.0634 (2) | |
N1 | 0.8059 (6) | 0.9078 (4) | 0.0277 (4) | 0.0575 (11) | |
N2 | 0.7951 (6) | 1.0006 (4) | 0.1014 (4) | 0.0615 (12) | |
N3 | 0.7671 (6) | 0.6478 (4) | 0.1269 (4) | 0.0629 (12) | |
N4 | 1.1558 (6) | 0.8307 (4) | 0.1705 (4) | 0.0634 (12) | |
O1 | 0.8960 (5) | 0.7176 (4) | −0.0538 (3) | 0.0702 (11) | |
O2 | 0.9122 (6) | 0.9257 (4) | 0.2316 (3) | 0.0765 (12) | |
O3 | 0.7074 (8) | 1.1752 (5) | 0.1680 (4) | 0.1100 (17) | |
H3 | 0.7013 | 1.1142 | 0.1242 | 0.165* | |
Br1 | 0.56036 (12) | 0.72427 (9) | −0.50503 (6) | 0.1092 (3) | |
Br2 | 0.88419 (11) | 0.51459 (8) | −0.23223 (6) | 0.0993 (3) | |
C1 | 0.6678 (8) | 0.7256 (7) | −0.3608 (5) | 0.0735 (17) | |
C2 | 0.7279 (8) | 0.6335 (6) | −0.3526 (5) | 0.0739 (17) | |
H2 | 0.7170 | 0.5750 | −0.4148 | 0.089* | |
C3 | 0.8027 (7) | 0.6351 (6) | −0.2480 (5) | 0.0640 (15) | |
C4 | 0.8237 (7) | 0.7221 (5) | −0.1492 (5) | 0.0554 (13) | |
C5 | 0.7518 (7) | 0.8070 (5) | −0.1654 (5) | 0.0560 (13) | |
C6 | 0.6762 (7) | 0.8066 (5) | −0.2717 (5) | 0.0633 (15) | |
H6 | 0.6312 | 0.8635 | −0.2805 | 0.076* | |
C7 | 0.7511 (7) | 0.8971 (5) | −0.0747 (5) | 0.0599 (14) | |
H7 | 0.7070 | 0.9520 | −0.0926 | 0.072* | |
C8 | 0.8578 (7) | 1.0033 (5) | 0.2049 (5) | 0.0619 (15) | |
C9 | 0.8605 (7) | 1.1010 (5) | 0.2936 (5) | 0.0650 (15) | |
C10 | 0.7878 (9) | 1.1828 (6) | 0.2710 (6) | 0.0816 (18) | |
C11 | 0.7928 (11) | 1.2694 (8) | 0.3564 (8) | 0.115 (3) | |
H11 | 0.7376 | 1.3193 | 0.3419 | 0.137* | |
C12 | 0.8784 (12) | 1.2853 (9) | 0.4653 (8) | 0.121 (3) | |
H12 | 0.8882 | 1.3489 | 0.5228 | 0.145* | |
C13 | 0.9489 (11) | 1.2042 (8) | 0.4860 (7) | 0.102 (2) | |
H13 | 1.0013 | 1.2104 | 0.5583 | 0.123* | |
C14 | 0.9418 (8) | 1.1170 (6) | 0.4024 (6) | 0.0783 (18) | |
H14 | 0.9933 | 1.0653 | 0.4181 | 0.094* | |
C15 | 0.7036 (9) | 0.6512 (6) | 0.2074 (6) | 0.087 (2) | |
H15 | 0.7133 | 0.7258 | 0.2499 | 0.104* | |
C16 | 0.6199 (11) | 0.5403 (11) | 0.2296 (9) | 0.132 (4) | |
H16 | 0.5737 | 0.5437 | 0.2861 | 0.159* | |
C17 | 0.6060 (12) | 0.4364 (8) | 0.1747 (10) | 0.112 (3) | |
H17 | 0.5520 | 0.3649 | 0.1908 | 0.135* | |
C18 | 0.6708 (11) | 0.4340 (7) | 0.0945 (9) | 0.110 (3) | |
H18 | 0.6646 | 0.3594 | 0.0549 | 0.132* | |
C19 | 0.7450 (9) | 0.5348 (6) | 0.0677 (6) | 0.084 (2) | |
H19 | 0.7824 | 0.5275 | 0.0072 | 0.101* | |
C20 | 1.2215 (9) | 0.8699 (6) | 0.2796 (6) | 0.0822 (19) | |
H20 | 1.1549 | 0.8861 | 0.3203 | 0.099* | |
C21 | 1.3818 (10) | 0.8873 (7) | 0.3343 (7) | 0.096 (2) | |
H21 | 1.4208 | 0.9102 | 0.4109 | 0.115* | |
C22 | 1.4841 (9) | 0.8712 (7) | 0.2773 (8) | 0.095 (2) | |
H22 | 1.5962 | 0.8866 | 0.3131 | 0.113* | |
C23 | 1.4190 (10) | 0.8330 (9) | 0.1689 (8) | 0.106 (3) | |
H23 | 1.4871 | 0.8211 | 0.1277 | 0.128* | |
C24 | 1.2535 (8) | 0.8101 (7) | 0.1146 (6) | 0.0843 (19) | |
H24 | 1.2104 | 0.7800 | 0.0380 | 0.101* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.0708 (5) | 0.0693 (5) | 0.0605 (5) | 0.0371 (4) | 0.0216 (4) | 0.0279 (4) |
N1 | 0.062 (3) | 0.051 (3) | 0.062 (3) | 0.025 (2) | 0.020 (2) | 0.021 (2) |
N2 | 0.070 (3) | 0.055 (3) | 0.062 (3) | 0.029 (2) | 0.022 (3) | 0.018 (2) |
N3 | 0.062 (3) | 0.071 (3) | 0.064 (3) | 0.032 (3) | 0.024 (3) | 0.027 (3) |
N4 | 0.066 (3) | 0.065 (3) | 0.063 (3) | 0.029 (3) | 0.019 (3) | 0.030 (3) |
O1 | 0.088 (3) | 0.080 (3) | 0.054 (2) | 0.050 (2) | 0.019 (2) | 0.024 (2) |
O2 | 0.106 (3) | 0.076 (3) | 0.061 (3) | 0.053 (3) | 0.024 (2) | 0.026 (2) |
O3 | 0.153 (5) | 0.108 (4) | 0.093 (4) | 0.092 (4) | 0.028 (4) | 0.024 (3) |
Br1 | 0.1322 (7) | 0.1456 (8) | 0.0597 (5) | 0.0755 (6) | 0.0172 (4) | 0.0387 (5) |
Br2 | 0.1300 (7) | 0.1115 (6) | 0.0806 (5) | 0.0829 (6) | 0.0316 (5) | 0.0252 (4) |
C1 | 0.070 (4) | 0.094 (5) | 0.058 (4) | 0.031 (4) | 0.019 (3) | 0.037 (4) |
C2 | 0.077 (4) | 0.081 (4) | 0.063 (4) | 0.033 (4) | 0.024 (3) | 0.019 (3) |
C3 | 0.062 (3) | 0.084 (4) | 0.058 (4) | 0.040 (3) | 0.022 (3) | 0.028 (3) |
C4 | 0.054 (3) | 0.052 (3) | 0.056 (4) | 0.017 (3) | 0.019 (3) | 0.018 (3) |
C5 | 0.053 (3) | 0.048 (3) | 0.062 (4) | 0.015 (3) | 0.016 (3) | 0.023 (3) |
C6 | 0.067 (4) | 0.065 (4) | 0.058 (4) | 0.025 (3) | 0.019 (3) | 0.028 (3) |
C7 | 0.064 (4) | 0.046 (3) | 0.068 (4) | 0.021 (3) | 0.015 (3) | 0.024 (3) |
C8 | 0.064 (4) | 0.057 (4) | 0.068 (4) | 0.023 (3) | 0.030 (3) | 0.022 (3) |
C9 | 0.063 (4) | 0.059 (4) | 0.068 (4) | 0.022 (3) | 0.024 (3) | 0.015 (3) |
C10 | 0.088 (5) | 0.075 (4) | 0.082 (5) | 0.041 (4) | 0.028 (4) | 0.013 (4) |
C11 | 0.132 (7) | 0.126 (7) | 0.111 (7) | 0.089 (6) | 0.047 (6) | 0.018 (6) |
C12 | 0.123 (7) | 0.153 (9) | 0.092 (7) | 0.071 (7) | 0.051 (6) | 0.005 (6) |
C13 | 0.116 (6) | 0.113 (6) | 0.074 (5) | 0.049 (5) | 0.038 (5) | 0.012 (5) |
C14 | 0.079 (4) | 0.090 (5) | 0.067 (5) | 0.038 (4) | 0.029 (4) | 0.017 (4) |
C15 | 0.092 (5) | 0.068 (4) | 0.092 (5) | 0.022 (4) | 0.048 (4) | 0.012 (4) |
C16 | 0.114 (7) | 0.176 (10) | 0.141 (9) | 0.046 (7) | 0.084 (7) | 0.099 (8) |
C17 | 0.100 (6) | 0.061 (5) | 0.156 (10) | 0.015 (5) | 0.033 (6) | 0.039 (6) |
C18 | 0.118 (7) | 0.069 (5) | 0.146 (9) | 0.041 (5) | 0.049 (6) | 0.032 (5) |
C19 | 0.098 (5) | 0.070 (5) | 0.102 (6) | 0.043 (4) | 0.047 (4) | 0.030 (4) |
C20 | 0.092 (5) | 0.097 (5) | 0.064 (4) | 0.054 (4) | 0.016 (4) | 0.025 (4) |
C21 | 0.100 (6) | 0.091 (5) | 0.078 (5) | 0.044 (5) | 0.002 (5) | 0.016 (4) |
C22 | 0.066 (5) | 0.092 (5) | 0.103 (7) | 0.025 (4) | 0.006 (5) | 0.028 (5) |
C23 | 0.078 (5) | 0.150 (8) | 0.106 (7) | 0.055 (5) | 0.038 (5) | 0.050 (6) |
C24 | 0.075 (5) | 0.116 (6) | 0.076 (5) | 0.048 (4) | 0.031 (4) | 0.037 (4) |
Geometric parameters (Å, º) top
Zn1—O1 | 1.976 (4) | C9—C14 | 1.381 (8) |
Zn1—N1 | 2.032 (4) | C9—C10 | 1.412 (9) |
Zn1—N3 | 2.057 (5) | C10—C11 | 1.358 (10) |
Zn1—N4 | 2.074 (5) | C11—C12 | 1.392 (11) |
Zn1—O2 | 2.077 (4) | C11—H11 | 0.93 |
N1—C7 | 1.281 (7) | C12—C13 | 1.385 (11) |
N1—N2 | 1.382 (6) | C12—H12 | 0.93 |
N2—C8 | 1.332 (7) | C13—C14 | 1.339 (10) |
N3—C15 | 1.310 (7) | C13—H13 | 0.93 |
N3—C19 | 1.360 (8) | C14—H14 | 0.93 |
N4—C24 | 1.319 (7) | C15—C16 | 1.423 (11) |
N4—C20 | 1.325 (8) | C15—H15 | 0.93 |
O1—C4 | 1.289 (6) | C16—C17 | 1.273 (13) |
O2—C8 | 1.279 (6) | C16—H16 | 0.93 |
O3—C10 | 1.342 (8) | C17—C18 | 1.314 (12) |
O3—H3 | 0.82 | C17—H17 | 0.93 |
Br1—C1 | 1.906 (6) | C18—C19 | 1.336 (10) |
Br2—C3 | 1.883 (6) | C18—H18 | 0.93 |
C1—C6 | 1.338 (9) | C19—H19 | 0.93 |
C1—C2 | 1.419 (8) | C20—C21 | 1.357 (9) |
C2—C3 | 1.372 (8) | C20—H20 | 0.93 |
C2—H2 | 0.93 | C21—C22 | 1.347 (10) |
C3—C4 | 1.428 (8) | C21—H21 | 0.93 |
C4—C5 | 1.423 (7) | C22—C23 | 1.317 (11) |
C5—C6 | 1.399 (7) | C22—H22 | 0.93 |
C5—C7 | 1.452 (8) | C23—C24 | 1.375 (9) |
C6—H6 | 0.93 | C23—H23 | 0.93 |
C7—H7 | 0.93 | C24—H24 | 0.93 |
C8—C9 | 1.478 (8) | | |
| | | |
O1—Zn1—N1 | 89.04 (17) | C14—C9—C8 | 119.6 (6) |
O1—Zn1—N3 | 96.67 (18) | C10—C9—C8 | 122.2 (6) |
N1—Zn1—N3 | 123.88 (17) | O3—C10—C11 | 118.4 (7) |
O1—Zn1—N4 | 94.43 (19) | O3—C10—C9 | 122.5 (6) |
N1—Zn1—N4 | 132.84 (17) | C11—C10—C9 | 119.1 (7) |
N3—Zn1—N4 | 102.42 (17) | C10—C11—C12 | 121.6 (8) |
O1—Zn1—O2 | 165.38 (15) | C10—C11—H11 | 119.2 |
N1—Zn1—O2 | 77.01 (17) | C12—C11—H11 | 119.2 |
N3—Zn1—O2 | 94.78 (18) | C13—C12—C11 | 118.4 (8) |
N4—Zn1—O2 | 91.95 (19) | C13—C12—H12 | 120.8 |
C7—N1—N2 | 116.7 (4) | C11—C12—H12 | 120.8 |
C7—N1—Zn1 | 127.3 (4) | C14—C13—C12 | 120.3 (8) |
N2—N1—Zn1 | 116.0 (3) | C14—C13—H13 | 119.8 |
C8—N2—N1 | 111.1 (4) | C12—C13—H13 | 119.8 |
C15—N3—C19 | 116.5 (5) | C13—C14—C9 | 122.2 (7) |
C15—N3—Zn1 | 123.4 (4) | C13—C14—H14 | 118.9 |
C19—N3—Zn1 | 120.1 (4) | C9—C14—H14 | 118.9 |
C24—N4—C20 | 117.5 (6) | N3—C15—C16 | 119.7 (7) |
C24—N4—Zn1 | 122.7 (4) | N3—C15—H15 | 120.2 |
C20—N4—Zn1 | 119.9 (4) | C16—C15—H15 | 120.2 |
C4—O1—Zn1 | 130.3 (4) | C17—C16—C15 | 122.3 (9) |
C8—O2—Zn1 | 111.6 (4) | C17—C16—H16 | 118.9 |
C10—O3—H3 | 109.5 | C15—C16—H16 | 118.9 |
C6—C1—C2 | 122.1 (6) | C16—C17—C18 | 117.6 (9) |
C6—C1—Br1 | 120.4 (5) | C16—C17—H17 | 121.2 |
C2—C1—Br1 | 117.4 (5) | C18—C17—H17 | 121.2 |
C3—C2—C1 | 116.5 (6) | C17—C18—C19 | 122.5 (8) |
C3—C2—H2 | 121.8 | C17—C18—H18 | 118.8 |
C1—C2—H2 | 121.8 | C19—C18—H18 | 118.8 |
C2—C3—C4 | 124.7 (5) | C18—C19—N3 | 121.4 (7) |
C2—C3—Br2 | 118.3 (5) | C18—C19—H19 | 119.3 |
C4—C3—Br2 | 117.0 (4) | N3—C19—H19 | 119.3 |
O1—C4—C5 | 124.2 (5) | N4—C20—C21 | 122.7 (7) |
O1—C4—C3 | 120.9 (5) | N4—C20—H20 | 118.6 |
C5—C4—C3 | 114.9 (5) | C21—C20—H20 | 118.6 |
C6—C5—C4 | 120.8 (5) | C22—C21—C20 | 119.8 (8) |
C6—C5—C7 | 116.4 (5) | C22—C21—H21 | 120.1 |
C4—C5—C7 | 122.8 (5) | C20—C21—H21 | 120.1 |
C1—C6—C5 | 120.9 (6) | C23—C22—C21 | 117.3 (7) |
C1—C6—H6 | 119.5 | C23—C22—H22 | 121.3 |
C5—C6—H6 | 119.5 | C21—C22—H22 | 121.3 |
N1—C7—C5 | 125.7 (5) | C22—C23—C24 | 122.2 (8) |
N1—C7—H7 | 117.1 | C22—C23—H23 | 118.9 |
C5—C7—H7 | 117.1 | C24—C23—H23 | 118.9 |
O2—C8—N2 | 124.2 (5) | N4—C24—C23 | 120.4 (7) |
O2—C8—C9 | 118.6 (5) | N4—C24—H24 | 119.8 |
N2—C8—C9 | 117.3 (5) | C23—C24—H24 | 119.8 |
C14—C9—C10 | 118.2 (6) | | |
| | | |
O1—Zn1—N1—C7 | 5.3 (5) | O1—C4—C5—C7 | −0.8 (8) |
N3—Zn1—N1—C7 | −92.0 (5) | C3—C4—C5—C7 | 176.1 (5) |
N4—Zn1—N1—C7 | 100.5 (5) | C2—C1—C6—C5 | 2.7 (9) |
O2—Zn1—N1—C7 | −179.1 (5) | Br1—C1—C6—C5 | 178.8 (4) |
O1—Zn1—N1—N2 | −174.8 (4) | C4—C5—C6—C1 | 0.8 (8) |
N3—Zn1—N1—N2 | 87.8 (4) | C7—C5—C6—C1 | −178.8 (5) |
N4—Zn1—N1—N2 | −79.6 (4) | N2—N1—C7—C5 | 179.5 (5) |
O2—Zn1—N1—N2 | 0.8 (3) | Zn1—N1—C7—C5 | −0.6 (8) |
C7—N1—N2—C8 | −179.2 (5) | C6—C5—C7—N1 | 176.2 (5) |
Zn1—N1—N2—C8 | 0.9 (5) | C4—C5—C7—N1 | −3.3 (8) |
O1—Zn1—N3—C15 | −165.6 (5) | Zn1—O2—C8—N2 | 4.3 (7) |
N1—Zn1—N3—C15 | −72.3 (6) | Zn1—O2—C8—C9 | −177.2 (4) |
N4—Zn1—N3—C15 | 98.3 (5) | N1—N2—C8—O2 | −3.6 (8) |
O2—Zn1—N3—C15 | 5.2 (5) | N1—N2—C8—C9 | 177.9 (4) |
O1—Zn1—N3—C19 | 18.4 (5) | O2—C8—C9—C14 | 8.8 (8) |
N1—Zn1—N3—C19 | 111.7 (5) | N2—C8—C9—C14 | −172.6 (5) |
N4—Zn1—N3—C19 | −77.7 (5) | O2—C8—C9—C10 | −173.7 (6) |
O2—Zn1—N3—C19 | −170.7 (5) | N2—C8—C9—C10 | 4.9 (8) |
O1—Zn1—N4—C24 | 10.3 (5) | C14—C9—C10—O3 | 179.5 (6) |
N1—Zn1—N4—C24 | −82.5 (6) | C8—C9—C10—O3 | 1.9 (10) |
N3—Zn1—N4—C24 | 108.1 (5) | C14—C9—C10—C11 | −3.3 (10) |
O2—Zn1—N4—C24 | −156.5 (5) | C8—C9—C10—C11 | 179.1 (6) |
O1—Zn1—N4—C20 | −169.2 (4) | O3—C10—C11—C12 | −177.9 (8) |
N1—Zn1—N4—C20 | 98.0 (5) | C9—C10—C11—C12 | 4.8 (13) |
N3—Zn1—N4—C20 | −71.3 (5) | C10—C11—C12—C13 | −4.8 (14) |
O2—Zn1—N4—C20 | 24.0 (5) | C11—C12—C13—C14 | 3.4 (13) |
N1—Zn1—O1—C4 | −9.6 (5) | C12—C13—C14—C9 | −2.2 (12) |
N3—Zn1—O1—C4 | 114.4 (5) | C10—C9—C14—C13 | 2.1 (10) |
N4—Zn1—O1—C4 | −142.5 (5) | C8—C9—C14—C13 | 179.7 (6) |
O2—Zn1—O1—C4 | −26.9 (10) | C19—N3—C15—C16 | 1.1 (10) |
O1—Zn1—O2—C8 | 15.3 (9) | Zn1—N3—C15—C16 | −175.0 (6) |
N1—Zn1—O2—C8 | −2.5 (4) | N3—C15—C16—C17 | 1.1 (14) |
N3—Zn1—O2—C8 | −126.2 (4) | C15—C16—C17—C18 | −0.8 (16) |
N4—Zn1—O2—C8 | 131.2 (4) | C16—C17—C18—C19 | −1.8 (16) |
C6—C1—C2—C3 | −3.0 (9) | C17—C18—C19—N3 | 4.1 (13) |
Br1—C1—C2—C3 | −179.2 (4) | C15—N3—C19—C18 | −3.6 (10) |
C1—C2—C3—C4 | −0.1 (9) | Zn1—N3—C19—C18 | 172.6 (6) |
C1—C2—C3—Br2 | 179.8 (4) | C24—N4—C20—C21 | −1.0 (10) |
Zn1—O1—C4—C5 | 8.9 (8) | Zn1—N4—C20—C21 | 178.5 (5) |
Zn1—O1—C4—C3 | −167.8 (4) | N4—C20—C21—C22 | 3.8 (11) |
C2—C3—C4—O1 | −179.8 (5) | C20—C21—C22—C23 | −3.2 (12) |
Br2—C3—C4—O1 | 0.3 (7) | C21—C22—C23—C24 | 0.1 (13) |
C2—C3—C4—C5 | 3.2 (8) | C20—N4—C24—C23 | −2.2 (10) |
Br2—C3—C4—C5 | −176.7 (4) | Zn1—N4—C24—C23 | 178.3 (6) |
O1—C4—C5—C6 | 179.6 (5) | C22—C23—C24—N4 | 2.7 (13) |
C3—C4—C5—C6 | −3.5 (7) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C24—H24···O1 | 0.93 | 2.53 | 3.073 (8) | 118 |
C20—H20···O2 | 0.93 | 2.46 | 3.022 (8) | 119 |
C19—H19···O1 | 0.93 | 2.56 | 3.108 (8) | 118 |
C15—H15···O2 | 0.93 | 2.55 | 3.110 (8) | 119 |
C14—H14···O2 | 0.93 | 2.46 | 2.779 (8) | 100 |
O3—H3···N2 | 0.82 | 1.87 | 2.582 (6) | 145 |