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In the title compound, [Zr(C8H5O5)2(C12H10N2)2]·H2O, each Zr atom is surrounded by four carboxylate O atoms of two 5-hydroxyisophthalate anions and two N atoms of two 1,2-di-4-pyridylethene ligands, the 5-hydroxyisophthalate anion functioning in a chelating coordination mode. The Zr atom is six-coordinate and the geometry is strongly distorted octahedral. The Zr cation and the water molecule lie on a crystallographic twofold axis.
Supporting information
CCDC reference: 269366
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.007 Å
- R factor = 0.064
- wR factor = 0.194
- Data-to-parameter ratio = 12.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for N2 - C8 .. 5.32 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Zr1 - O1 .. 5.58 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Zr1 - O2 .. 5.56 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Zr1 - N1 .. 7.34 su
PLAT731_ALERT_1_C Bond Calc 0.82(14), Rep 0.82(5) ...... 2.80 su-Rat
O6 -H6A 1.555 1.555
PLAT804_ALERT_4_C ARU-Pack Problem in PLATON Analysis ............ !
PLAT804_ALERT_4_C ARU-Pack Problem in PLATON Analysis ............ !
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 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
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Bruker, 2002) and ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXTL (Bruker, 2002).
Bis(1,2-di-4-pyridylethene)bis(5-hydroxylisophthalato)zirconium(II) monohydrate
top
Crystal data top
[Zr(C8H5O5)2(C12H10N2)2]·H2O | F(000) = 1712 |
Mr = 835.92 | Dx = 1.538 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 3197 reflections |
a = 34.037 (3) Å | θ = 1.2–25.1° |
b = 8.3818 (7) Å | µ = 0.38 mm−1 |
c = 13.0137 (11) Å | T = 298 K |
β = 103.502 (1)° | Prism, colorless |
V = 3610.1 (5) Å3 | 0.33 × 0.30 × 0.07 mm |
Z = 4 | |
Data collection top
Bruker SMART APEX area-detector diffractometer | 3197 independent reflections |
Radiation source: fine-focus sealed tube | 2859 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
φ and ω scans | θmax = 25.1°, θmin = 1.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −31→40 |
Tmin = 0.88, Tmax = 0.97 | k = −8→10 |
9198 measured reflections | l = −15→14 |
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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.194 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.12 | w = 1/[σ2(Fo2) + (0.1021P)2 + 20.1938P] where P = (Fo2 + 2Fc2)/3 |
3197 reflections | (Δ/σ)max < 0.001 |
259 parameters | Δρmax = 0.83 e Å−3 |
1 restraint | Δρmin = −0.48 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 | |
Zr1 | 1.0000 | 0.85993 (8) | 0.7500 | 0.0337 (3) | |
C1 | 0.93129 (15) | 0.6407 (6) | 0.7424 (4) | 0.0329 (11) | |
H1 | 0.9271 | 0.6646 | 0.6708 | 0.039* | |
C2 | 0.90451 (14) | 0.5402 (6) | 0.7730 (4) | 0.0346 (11) | |
H2 | 0.8826 | 0.4990 | 0.7237 | 0.042* | |
C3 | 0.91079 (13) | 0.5001 (6) | 0.8805 (4) | 0.0299 (10) | |
C4 | 0.94406 (14) | 0.5663 (6) | 0.9484 (4) | 0.0330 (11) | |
H4 | 0.9498 | 0.5414 | 1.0200 | 0.040* | |
C5 | 0.96882 (14) | 0.6691 (6) | 0.9103 (4) | 0.0311 (10) | |
H5A | 0.9906 | 0.7146 | 0.9579 | 0.037* | |
C6 | 0.88295 (15) | 0.3974 (6) | 0.9203 (4) | 0.0343 (11) | |
H6 | 0.8905 | 0.3696 | 0.9914 | 0.041* | |
C7 | 0.84832 (15) | 0.3405 (6) | 0.8657 (4) | 0.0347 (11) | |
H7 | 0.8411 | 0.3656 | 0.7942 | 0.042* | |
C8 | 0.75863 (16) | 0.0886 (7) | 0.8825 (5) | 0.0493 (15) | |
H8 | 0.7351 | 0.0508 | 0.8374 | 0.059* | |
C9 | 0.78545 (15) | 0.1861 (7) | 0.8400 (5) | 0.0439 (13) | |
H9 | 0.7796 | 0.2118 | 0.7685 | 0.053* | |
C10 | 0.82002 (14) | 0.2410 (5) | 0.9071 (4) | 0.0345 (11) | |
C11 | 0.82627 (15) | 0.1959 (6) | 1.0134 (4) | 0.0385 (12) | |
H11 | 0.8492 | 0.2311 | 1.0620 | 0.046* | |
C12 | 0.79913 (16) | 0.1010 (6) | 1.0463 (5) | 0.0436 (13) | |
H12 | 0.8044 | 0.0711 | 1.1170 | 0.052* | |
C13 | 0.90786 (13) | 1.0888 (5) | 0.5469 (3) | 0.0245 (9) | |
C14 | 0.87853 (13) | 1.1902 (5) | 0.5680 (4) | 0.0267 (10) | |
H14 | 0.8804 | 1.2265 | 0.6365 | 0.032* | |
C15 | 0.84651 (13) | 1.2374 (5) | 0.4874 (4) | 0.0263 (10) | |
C16 | 0.84390 (13) | 1.1854 (6) | 0.3851 (4) | 0.0290 (10) | |
H16 | 0.8222 | 1.2163 | 0.3310 | 0.035* | |
C17 | 0.87377 (14) | 1.0869 (6) | 0.3637 (4) | 0.0275 (10) | |
C18 | 0.90550 (13) | 1.0377 (5) | 0.4435 (3) | 0.0245 (9) | |
H18 | 0.9253 | 0.9707 | 0.4287 | 0.029* | |
C19 | 0.94090 (13) | 1.0309 (5) | 0.6359 (4) | 0.0274 (10) | |
C20 | 0.81537 (15) | 1.3449 (6) | 0.5165 (4) | 0.0366 (12) | |
O1 | 0.96667 (10) | 0.9355 (4) | 0.6136 (3) | 0.0360 (8) | |
O2 | 0.94209 (10) | 1.0725 (4) | 0.7284 (3) | 0.0375 (8) | |
O3 | 0.82011 (13) | 1.4007 (5) | 0.6036 (3) | 0.0564 (12) | |
O4 | 0.78401 (11) | 1.3709 (5) | 0.4397 (3) | 0.0485 (10) | |
H4A | 0.7682 | 1.4301 | 0.4602 | 0.073* | |
O5 | 0.87005 (11) | 1.0387 (5) | 0.2611 (3) | 0.0417 (9) | |
H5 | 0.8904 | 0.9897 | 0.2563 | 0.063* | |
N1 | 0.96296 (10) | 0.7065 (4) | 0.8083 (3) | 0.0241 (8) | |
N2 | 0.76607 (13) | 0.0505 (5) | 0.9828 (4) | 0.0445 (11) | |
O6 | 0.0000 | 0.3508 (11) | 0.7500 | 0.158 (7) | |
H6A | 0.019 (4) | 0.326 (19) | 0.724 (15) | 0.237* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zr1 | 0.0273 (4) | 0.0366 (4) | 0.0376 (4) | 0.000 | 0.0086 (3) | 0.000 |
C1 | 0.033 (3) | 0.039 (3) | 0.028 (2) | −0.010 (2) | 0.010 (2) | −0.001 (2) |
C2 | 0.030 (2) | 0.036 (3) | 0.037 (3) | −0.011 (2) | 0.006 (2) | −0.005 (2) |
C3 | 0.026 (2) | 0.027 (2) | 0.038 (3) | −0.0022 (19) | 0.0101 (19) | 0.002 (2) |
C4 | 0.028 (2) | 0.039 (3) | 0.031 (2) | −0.003 (2) | 0.0059 (19) | 0.005 (2) |
C5 | 0.023 (2) | 0.032 (2) | 0.037 (3) | −0.0054 (19) | 0.0047 (19) | 0.001 (2) |
C6 | 0.033 (3) | 0.035 (3) | 0.036 (3) | −0.011 (2) | 0.009 (2) | 0.006 (2) |
C7 | 0.030 (3) | 0.035 (3) | 0.041 (3) | −0.006 (2) | 0.014 (2) | 0.004 (2) |
C8 | 0.024 (3) | 0.047 (3) | 0.070 (4) | −0.008 (2) | −0.003 (3) | −0.012 (3) |
C9 | 0.030 (3) | 0.043 (3) | 0.057 (3) | −0.008 (2) | 0.007 (2) | 0.002 (3) |
C10 | 0.025 (2) | 0.023 (2) | 0.059 (3) | −0.0039 (19) | 0.017 (2) | −0.001 (2) |
C11 | 0.033 (3) | 0.040 (3) | 0.046 (3) | −0.007 (2) | 0.015 (2) | 0.001 (2) |
C12 | 0.037 (3) | 0.040 (3) | 0.056 (3) | −0.005 (2) | 0.016 (3) | 0.007 (3) |
C13 | 0.023 (2) | 0.022 (2) | 0.031 (2) | −0.0011 (17) | 0.0107 (18) | 0.0037 (18) |
C14 | 0.029 (2) | 0.023 (2) | 0.032 (2) | 0.0018 (18) | 0.0156 (19) | 0.0005 (18) |
C15 | 0.022 (2) | 0.023 (2) | 0.036 (2) | 0.0039 (18) | 0.0122 (18) | 0.0044 (18) |
C16 | 0.021 (2) | 0.032 (2) | 0.033 (2) | 0.0058 (18) | 0.0041 (18) | 0.0045 (19) |
C17 | 0.030 (2) | 0.027 (2) | 0.027 (2) | −0.0002 (19) | 0.0117 (18) | −0.0001 (18) |
C18 | 0.021 (2) | 0.023 (2) | 0.032 (2) | 0.0056 (17) | 0.0119 (18) | 0.0016 (18) |
C19 | 0.021 (2) | 0.028 (2) | 0.034 (3) | −0.0035 (18) | 0.0080 (18) | 0.0083 (19) |
C20 | 0.029 (3) | 0.029 (3) | 0.055 (3) | 0.010 (2) | 0.016 (2) | 0.008 (2) |
O1 | 0.0284 (17) | 0.047 (2) | 0.0335 (18) | 0.0140 (16) | 0.0084 (14) | 0.0115 (15) |
O2 | 0.0352 (19) | 0.046 (2) | 0.0298 (18) | −0.0015 (16) | 0.0052 (14) | −0.0003 (15) |
O3 | 0.052 (2) | 0.072 (3) | 0.047 (2) | 0.030 (2) | 0.0145 (19) | −0.014 (2) |
O4 | 0.033 (2) | 0.051 (2) | 0.062 (3) | 0.0199 (17) | 0.0119 (18) | −0.0045 (19) |
O5 | 0.039 (2) | 0.060 (2) | 0.0254 (17) | 0.0122 (18) | 0.0053 (14) | −0.0086 (16) |
N1 | 0.0183 (17) | 0.0245 (18) | 0.032 (2) | −0.0020 (15) | 0.0108 (15) | −0.0005 (16) |
N2 | 0.039 (3) | 0.039 (2) | 0.058 (3) | −0.002 (2) | 0.016 (2) | 0.008 (2) |
O6 | 0.090 (8) | 0.047 (5) | 0.34 (2) | 0.000 | 0.064 (10) | 0.000 |
Geometric parameters (Å, º) top
Zr1—O1 | 1.975 (3) | C9—C10 | 1.371 (7) |
Zr1—O1i | 1.975 (3) | C9—H9 | 0.9300 |
Zr1—N1i | 2.066 (3) | C10—C11 | 1.402 (7) |
Zr1—N1 | 2.066 (3) | C11—C12 | 1.361 (7) |
Zr1—O2i | 2.623 (4) | C11—H11 | 0.9300 |
Zr1—O2 | 2.623 (4) | C12—N2 | 1.301 (7) |
Zr1—C19i | 2.629 (4) | C12—H12 | 0.9300 |
Zr1—C19 | 2.629 (4) | C13—C14 | 1.386 (6) |
C1—N1 | 1.331 (6) | C13—C18 | 1.396 (6) |
C1—C2 | 1.367 (7) | C13—C19 | 1.495 (6) |
C1—H1 | 0.9300 | C14—C15 | 1.382 (6) |
C2—C3 | 1.405 (7) | C14—H14 | 0.9300 |
C2—H2 | 0.9300 | C15—C16 | 1.384 (7) |
C3—C4 | 1.380 (7) | C15—C20 | 1.506 (6) |
C3—C6 | 1.462 (6) | C16—C17 | 1.388 (7) |
C4—C5 | 1.376 (7) | C16—H16 | 0.9300 |
C4—H4 | 0.9300 | C17—O5 | 1.372 (5) |
C5—N1 | 1.332 (6) | C17—C18 | 1.375 (6) |
C5—H5A | 0.9300 | C18—H18 | 0.9300 |
C6—C7 | 1.316 (7) | C19—O2 | 1.245 (6) |
C6—H6 | 0.9300 | C19—O1 | 1.269 (6) |
C7—C10 | 1.468 (6) | C20—O3 | 1.201 (7) |
C7—H7 | 0.9300 | C20—O4 | 1.299 (7) |
C8—N2 | 1.310 (8) | O4—H4A | 0.8200 |
C8—C9 | 1.430 (8) | O5—H5 | 0.8200 |
C8—H8 | 0.9300 | O6—H6A | 0.82 (5) |
| | | |
O1—Zr1—O1i | 142.6 (2) | N2—C8—H8 | 118.9 |
O1—Zr1—N1i | 98.12 (14) | C9—C8—H8 | 118.9 |
O1i—Zr1—N1i | 104.97 (14) | C10—C9—C8 | 118.4 (5) |
O1—Zr1—N1 | 104.97 (14) | C10—C9—H9 | 120.8 |
O1i—Zr1—N1 | 98.12 (14) | C8—C9—H9 | 120.8 |
N1i—Zr1—N1 | 103.0 (2) | C9—C10—C11 | 116.6 (5) |
O1—Zr1—O2i | 97.92 (13) | C9—C10—C7 | 119.7 (5) |
O1i—Zr1—O2i | 54.99 (12) | C11—C10—C7 | 123.6 (5) |
N1i—Zr1—O2i | 87.38 (13) | C12—C11—C10 | 120.7 (5) |
N1—Zr1—O2i | 153.06 (13) | C12—C11—H11 | 119.7 |
O1—Zr1—O2 | 54.99 (12) | C10—C11—H11 | 119.7 |
O1i—Zr1—O2 | 97.93 (13) | N2—C12—C11 | 122.7 (6) |
N1i—Zr1—O2 | 153.06 (13) | N2—C12—H12 | 118.6 |
N1—Zr1—O2 | 87.38 (13) | C11—C12—H12 | 118.6 |
O2i—Zr1—O2 | 94.44 (16) | C14—C13—C18 | 119.8 (4) |
O1—Zr1—C19i | 122.42 (15) | C14—C13—C19 | 119.5 (4) |
O1i—Zr1—C19i | 27.63 (14) | C18—C13—C19 | 120.7 (4) |
N1i—Zr1—C19i | 95.44 (13) | C15—C14—C13 | 120.2 (4) |
N1—Zr1—C19i | 125.74 (14) | C15—C14—H14 | 119.9 |
O2i—Zr1—C19i | 27.43 (12) | C13—C14—H14 | 119.9 |
O2—Zr1—C19i | 98.45 (12) | C14—C15—C16 | 120.1 (4) |
O1—Zr1—C19 | 27.63 (14) | C14—C15—C20 | 117.2 (4) |
O1i—Zr1—C19 | 122.42 (15) | C16—C15—C20 | 122.6 (4) |
N1i—Zr1—C19 | 125.74 (14) | C15—C16—C17 | 119.7 (4) |
N1—Zr1—C19 | 95.44 (13) | C15—C16—H16 | 120.2 |
O2i—Zr1—C19 | 98.45 (12) | C17—C16—H16 | 120.2 |
O2—Zr1—C19 | 27.43 (12) | O5—C17—C18 | 121.6 (4) |
C19i—Zr1—C19 | 113.9 (2) | O5—C17—C16 | 117.7 (4) |
N1—C1—C2 | 124.2 (4) | C18—C17—C16 | 120.6 (4) |
N1—C1—H1 | 117.9 | C17—C18—C13 | 119.6 (4) |
C2—C1—H1 | 117.9 | C17—C18—H18 | 120.2 |
C1—C2—C3 | 118.7 (4) | C13—C18—H18 | 120.2 |
C1—C2—H2 | 120.6 | O2—C19—O1 | 122.0 (4) |
C3—C2—H2 | 120.6 | O2—C19—C13 | 120.5 (4) |
C4—C3—C2 | 116.9 (4) | O1—C19—C13 | 117.5 (4) |
C4—C3—C6 | 120.8 (4) | O2—C19—Zr1 | 76.0 (3) |
C2—C3—C6 | 122.2 (4) | O1—C19—Zr1 | 46.2 (2) |
C5—C4—C3 | 120.0 (4) | C13—C19—Zr1 | 162.4 (3) |
C5—C4—H4 | 120.0 | O3—C20—O4 | 124.5 (5) |
C3—C4—H4 | 120.0 | O3—C20—C15 | 121.5 (5) |
N1—C5—C4 | 123.0 (4) | O4—C20—C15 | 114.0 (5) |
N1—C5—H5A | 118.5 | C19—O1—Zr1 | 106.2 (3) |
C4—C5—H5A | 118.5 | C19—O2—Zr1 | 76.5 (3) |
C7—C6—C3 | 126.5 (5) | C20—O4—H4A | 109.5 |
C7—C6—H6 | 116.7 | C17—O5—H5 | 109.5 |
C3—C6—H6 | 116.7 | C1—N1—C5 | 117.1 (4) |
C6—C7—C10 | 126.1 (5) | C1—N1—Zr1 | 119.5 (3) |
C6—C7—H7 | 116.9 | C5—N1—Zr1 | 123.4 (3) |
C10—C7—H7 | 116.9 | C12—N2—C8 | 119.4 (5) |
N2—C8—C9 | 122.2 (5) | | |
| | | |
N1—C1—C2—C3 | −1.2 (8) | O1—Zr1—C19—C13 | 25.3 (9) |
C1—C2—C3—C4 | 0.0 (7) | O1i—Zr1—C19—C13 | 169.9 (9) |
C1—C2—C3—C6 | 178.1 (5) | N1i—Zr1—C19—C13 | 23.4 (10) |
C2—C3—C4—C5 | 1.4 (7) | N1—Zr1—C19—C13 | −86.9 (10) |
C6—C3—C4—C5 | −176.7 (5) | O2i—Zr1—C19—C13 | 116.3 (10) |
C3—C4—C5—N1 | −1.8 (8) | O2—Zr1—C19—C13 | −160.4 (11) |
C4—C3—C6—C7 | 172.8 (5) | C19i—Zr1—C19—C13 | 140.0 (10) |
C2—C3—C6—C7 | −5.2 (8) | C14—C15—C20—O3 | 7.4 (7) |
C3—C6—C7—C10 | −178.2 (5) | C16—C15—C20—O3 | −172.9 (5) |
N2—C8—C9—C10 | 0.0 (9) | C14—C15—C20—O4 | −173.1 (4) |
C8—C9—C10—C11 | 0.1 (8) | C16—C15—C20—O4 | 6.7 (7) |
C8—C9—C10—C7 | 179.5 (5) | O2—C19—O1—Zr1 | 6.6 (5) |
C6—C7—C10—C9 | −178.1 (5) | C13—C19—O1—Zr1 | −171.6 (3) |
C6—C7—C10—C11 | 1.3 (8) | O1i—Zr1—O1—C19 | −53.6 (3) |
C9—C10—C11—C12 | 0.6 (8) | N1i—Zr1—O1—C19 | 178.4 (3) |
C7—C10—C11—C12 | −178.8 (5) | N1—Zr1—O1—C19 | 72.6 (3) |
C10—C11—C12—N2 | −1.5 (9) | O2i—Zr1—O1—C19 | −93.1 (3) |
C18—C13—C14—C15 | 1.6 (6) | O2—Zr1—O1—C19 | −3.2 (3) |
C19—C13—C14—C15 | −176.2 (4) | C19i—Zr1—O1—C19 | −79.8 (4) |
C13—C14—C15—C16 | −0.9 (7) | O1—C19—O2—Zr1 | −4.9 (4) |
C13—C14—C15—C20 | 178.8 (4) | C13—C19—O2—Zr1 | 173.2 (4) |
C14—C15—C16—C17 | −0.6 (7) | O1—Zr1—O2—C19 | 3.2 (3) |
C20—C15—C16—C17 | 179.7 (4) | O1i—Zr1—O2—C19 | 155.1 (3) |
C15—C16—C17—O5 | −179.7 (4) | N1i—Zr1—O2—C19 | 6.9 (4) |
C15—C16—C17—C18 | 1.4 (7) | N1—Zr1—O2—C19 | −107.1 (3) |
O5—C17—C18—C13 | −179.5 (4) | O2i—Zr1—O2—C19 | 99.8 (3) |
C16—C17—C18—C13 | −0.7 (7) | C19i—Zr1—O2—C19 | 127.1 (3) |
C14—C13—C18—C17 | −0.8 (6) | C2—C1—N1—C5 | 0.9 (7) |
C19—C13—C18—C17 | 177.0 (4) | C2—C1—N1—Zr1 | −178.7 (4) |
C14—C13—C19—O2 | 0.3 (6) | C4—C5—N1—C1 | 0.6 (7) |
C18—C13—C19—O2 | −177.5 (4) | C4—C5—N1—Zr1 | −179.8 (4) |
C14—C13—C19—O1 | 178.5 (4) | O1—Zr1—N1—C1 | 21.3 (4) |
C18—C13—C19—O1 | 0.7 (6) | O1i—Zr1—N1—C1 | 171.6 (3) |
C14—C13—C19—Zr1 | 158.1 (8) | N1i—Zr1—N1—C1 | −80.9 (3) |
C18—C13—C19—Zr1 | −19.7 (12) | O2i—Zr1—N1—C1 | 168.6 (3) |
O1—Zr1—C19—O2 | −174.3 (5) | O2—Zr1—N1—C1 | 73.9 (3) |
O1i—Zr1—C19—O2 | −29.7 (3) | C19i—Zr1—N1—C1 | 172.5 (3) |
N1i—Zr1—C19—O2 | −176.2 (2) | C19—Zr1—N1—C1 | 47.7 (4) |
N1—Zr1—C19—O2 | 73.6 (3) | O1—Zr1—N1—C5 | −158.3 (4) |
O2i—Zr1—C19—O2 | −83.3 (3) | O1i—Zr1—N1—C5 | −8.0 (4) |
C19i—Zr1—C19—O2 | −59.6 (2) | N1i—Zr1—N1—C5 | 99.5 (4) |
O1i—Zr1—C19—O1 | 144.6 (3) | O2i—Zr1—N1—C5 | −11.0 (5) |
N1i—Zr1—C19—O1 | −1.9 (4) | O2—Zr1—N1—C5 | −105.7 (4) |
N1—Zr1—C19—O1 | −112.2 (3) | C19i—Zr1—N1—C5 | −7.1 (4) |
O2i—Zr1—C19—O1 | 91.0 (3) | C19—Zr1—N1—C5 | −131.9 (4) |
O2—Zr1—C19—O1 | 174.3 (5) | C11—C12—N2—C8 | 1.6 (9) |
C19i—Zr1—C19—O1 | 114.6 (3) | C9—C8—N2—C12 | −0.9 (9) |
Symmetry code: (i) −x+2, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6A···O2ii | 0.82 (14) | 2.50 (15) | 3.024 (8) | 122 (15) |
O5—H5···O2iii | 0.82 | 1.95 | 2.747 (5) | 164 |
O4—H4A···N2iv | 0.82 | 1.83 | 2.644 (6) | 175 |
Symmetry codes: (ii) −x+1, y−1, −z+3/2; (iii) x, −y+2, z−1/2; (iv) −x+3/2, y+3/2, −z+3/2. |
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