In the title compound, [Zn
2(C
6H
8O
4)
2(C
12H
8N
2)
2(H
2O)
2], each Zn atom is six-coordinated in the ZnO
4N
2 form in a distorted tetragonal–bipyramidal geometry. The water molecules act as donors in O—H
O hydrogen bonds, connecting the molecules into chains. The packing is further stabilized by intermolecular C—H
O interactions.
Supporting information
CCDC reference: 262271
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
Some non-H atoms missing
- R factor = 0.024
- wR factor = 0.065
- Data-to-parameter ratio = 13.3
checkCIF/PLATON results
No syntax errors found
Datablock: I
Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Zn1 - O3 .. 30.48 su
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Zn1 - O4 .. 10.94 su
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Zn1 - N2 .. 6.17 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O3
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
12 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 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
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
di-µ-adipato-
κ6O,
O':
O'';
O:
O',
O''-bis[aqua(1,10-phenanthroline-
κ2N,
N')zinc(II)]
top
Crystal data top
[Zn2(C6H8O4)2(C12H8N2)2(H2O)2] | Z = 1 |
Mr = 407.71 | F(000) = 420 |
Triclinic, P1 | Dx = 1.609 Mg m−3 |
a = 8.1984 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.7549 (5) Å | Cell parameters from 3889 reflections |
c = 11.8636 (6) Å | θ = 2.3–26.0° |
α = 70.971 (1)° | µ = 1.49 mm−1 |
β = 75.508 (1)° | T = 293 K |
γ = 72.077 (1)° | Plate, pink |
V = 841.48 (7) Å3 | 0.54 × 0.15 × 0.08 mm |
Data collection top
Siemens SMART 1000 CCD area-detector diffractometer | 3228 independent reflections |
Radiation source: fine-focus sealed tube | 3094 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.009 |
Detector resolution: 8.33 pixels mm-1 | θmax = 26.0°, θmin = 2.3° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −10→12 |
Tmin = 0.500, Tmax = 0.890 | l = −14→13 |
4743 measured reflections | |
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)] = 0.024 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.065 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0373P)2 + 0.2537P] where P = (Fo2 + 2Fc2)/3 |
3228 reflections | (Δ/σ)max = 0.001 |
243 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.27 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 | 0.06374 (2) | 0.14741 (2) | 0.291440 (15) | 0.03325 (8) | |
O1W | −0.07073 (18) | −0.01149 (15) | 0.38210 (11) | 0.0366 (3) | |
O4 | 0.26164 (16) | 0.08574 (15) | 0.39055 (11) | 0.0408 (3) | |
O1 | −0.1033 (2) | 0.31354 (17) | 0.35850 (14) | 0.0563 (4) | |
O3 | 0.3049 (2) | 0.26808 (15) | 0.22882 (12) | 0.0522 (3) | |
N2 | −0.02543 (19) | 0.25473 (16) | 0.12310 (13) | 0.0355 (3) | |
N1 | 0.22272 (18) | 0.00009 (16) | 0.17503 (12) | 0.0350 (3) | |
C11 | 0.0567 (2) | 0.18910 (19) | 0.03249 (14) | 0.0342 (3) | |
C16 | 0.3447 (2) | 0.18388 (18) | 0.32699 (15) | 0.0336 (3) | |
O2 | −0.1077 (2) | 0.28558 (16) | 0.55299 (13) | 0.0629 (4) | |
C12 | 0.1889 (2) | 0.05181 (19) | 0.06083 (14) | 0.0335 (3) | |
C7 | 0.0164 (3) | 0.2490 (2) | −0.08530 (15) | 0.0435 (4) | |
C17 | 0.4907 (2) | 0.1959 (2) | 0.37621 (17) | 0.0390 (4) | |
H17A | 0.5575 | 0.2591 | 0.3132 | 0.047* | |
H17B | 0.5676 | 0.0973 | 0.4002 | 0.047* | |
C13 | −0.1442 (2) | 0.35907 (19) | 0.45197 (16) | 0.0376 (4) | |
C4 | 0.2760 (2) | −0.0217 (2) | −0.02960 (16) | 0.0423 (4) | |
C14 | −0.2486 (3) | 0.5204 (2) | 0.43380 (17) | 0.0454 (4) | |
H14B | −0.1790 | 0.5831 | 0.3729 | 0.055* | |
H14A | −0.3508 | 0.5313 | 0.4014 | 0.055* | |
C18 | 0.4225 (2) | 0.2612 (2) | 0.48479 (17) | 0.0397 (4) | |
H18A | 0.3566 | 0.1969 | 0.5475 | 0.060* | |
H18B | 0.5207 | 0.2607 | 0.5167 | 0.060* | |
C15 | −0.3078 (2) | 0.58025 (19) | 0.54365 (16) | 0.0395 (4) | |
H15A | −0.2069 | 0.5794 | 0.5728 | 0.059* | |
H15B | −0.3719 | 0.5155 | 0.6074 | 0.059* | |
C1 | 0.3435 (2) | −0.1258 (2) | 0.20292 (17) | 0.0434 (4) | |
H1 | 0.3666 | −0.1625 | 0.2817 | 0.052* | |
C10 | −0.1483 (3) | 0.3810 (2) | 0.09853 (18) | 0.0469 (4) | |
H10 | −0.2062 | 0.4263 | 0.1603 | 0.056* | |
C6 | 0.1056 (3) | 0.1687 (3) | −0.17407 (17) | 0.0533 (5) | |
H6 | 0.0778 | 0.2062 | −0.2516 | 0.064* | |
C5 | 0.2281 (3) | 0.0410 (3) | −0.14757 (17) | 0.0541 (5) | |
H5 | 0.2836 | −0.0084 | −0.2072 | 0.065* | |
C3 | 0.4046 (3) | −0.1541 (2) | 0.00321 (19) | 0.0516 (5) | |
H3 | 0.4668 | −0.2062 | −0.0536 | 0.062* | |
C8 | −0.1118 (3) | 0.3834 (2) | −0.10763 (19) | 0.0545 (5) | |
H8 | −0.1407 | 0.4280 | −0.1846 | 0.065* | |
C9 | −0.1941 (3) | 0.4486 (2) | −0.0164 (2) | 0.0563 (5) | |
H9 | −0.2801 | 0.5375 | −0.0305 | 0.068* | |
C2 | 0.4379 (3) | −0.2060 (2) | 0.1190 (2) | 0.0531 (5) | |
H2 | 0.5225 | −0.2938 | 0.1417 | 0.064* | |
H1WB | −0.141 (3) | 0.002 (3) | 0.437 (2) | 0.055 (7)* | |
H1WA | −0.005 (3) | −0.099 (3) | 0.403 (2) | 0.061 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.03840 (13) | 0.03370 (12) | 0.02642 (11) | −0.00101 (8) | −0.00770 (8) | −0.01219 (8) |
O1W | 0.0400 (7) | 0.0387 (7) | 0.0274 (6) | −0.0051 (5) | −0.0041 (5) | −0.0095 (5) |
O4 | 0.0419 (7) | 0.0511 (7) | 0.0321 (6) | −0.0148 (6) | −0.0034 (5) | −0.0137 (5) |
O1 | 0.0592 (9) | 0.0546 (8) | 0.0557 (9) | 0.0121 (7) | −0.0151 (7) | −0.0361 (7) |
O3 | 0.0701 (9) | 0.0433 (7) | 0.0408 (7) | −0.0065 (6) | −0.0218 (7) | −0.0061 (6) |
N2 | 0.0411 (8) | 0.0337 (7) | 0.0306 (7) | −0.0081 (6) | −0.0073 (6) | −0.0076 (6) |
N1 | 0.0370 (7) | 0.0375 (7) | 0.0300 (7) | −0.0074 (6) | −0.0019 (5) | −0.0129 (6) |
C11 | 0.0418 (9) | 0.0391 (9) | 0.0259 (8) | −0.0191 (7) | −0.0054 (6) | −0.0061 (7) |
C16 | 0.0330 (8) | 0.0337 (8) | 0.0323 (8) | 0.0024 (6) | −0.0036 (6) | −0.0179 (7) |
O2 | 0.0902 (12) | 0.0378 (7) | 0.0420 (8) | 0.0069 (7) | −0.0063 (7) | −0.0110 (6) |
C12 | 0.0396 (9) | 0.0392 (9) | 0.0266 (8) | −0.0183 (7) | 0.0015 (6) | −0.0123 (7) |
C7 | 0.0572 (11) | 0.0524 (11) | 0.0289 (9) | −0.0303 (9) | −0.0099 (8) | −0.0035 (8) |
C17 | 0.0323 (8) | 0.0394 (9) | 0.0456 (10) | −0.0001 (7) | −0.0061 (7) | −0.0204 (8) |
C13 | 0.0368 (9) | 0.0340 (9) | 0.0413 (9) | −0.0059 (7) | 0.0001 (7) | −0.0170 (7) |
C4 | 0.0501 (10) | 0.0498 (10) | 0.0351 (9) | −0.0258 (9) | 0.0081 (8) | −0.0207 (8) |
C14 | 0.0616 (12) | 0.0329 (9) | 0.0374 (9) | −0.0016 (8) | −0.0067 (8) | −0.0143 (7) |
C18 | 0.0427 (9) | 0.0368 (9) | 0.0423 (10) | −0.0007 (7) | −0.0151 (7) | −0.0167 (7) |
C15 | 0.0425 (9) | 0.0350 (9) | 0.0401 (9) | −0.0002 (7) | −0.0094 (7) | −0.0158 (7) |
C1 | 0.0431 (10) | 0.0426 (10) | 0.0403 (10) | −0.0036 (8) | −0.0047 (7) | −0.0137 (8) |
C10 | 0.0512 (11) | 0.0386 (9) | 0.0455 (10) | −0.0053 (8) | −0.0124 (8) | −0.0067 (8) |
C6 | 0.0785 (15) | 0.0691 (14) | 0.0253 (9) | −0.0424 (12) | −0.0057 (9) | −0.0096 (9) |
C5 | 0.0761 (14) | 0.0713 (14) | 0.0303 (9) | −0.0399 (12) | 0.0087 (9) | −0.0267 (9) |
C3 | 0.0546 (11) | 0.0538 (12) | 0.0509 (12) | −0.0178 (9) | 0.0121 (9) | −0.0318 (10) |
C8 | 0.0681 (13) | 0.0558 (12) | 0.0396 (10) | −0.0242 (10) | −0.0252 (10) | 0.0075 (9) |
C9 | 0.0603 (13) | 0.0457 (11) | 0.0548 (13) | −0.0082 (9) | −0.0239 (10) | 0.0033 (9) |
C2 | 0.0456 (11) | 0.0456 (11) | 0.0644 (13) | −0.0033 (8) | 0.0020 (9) | −0.0260 (10) |
Geometric parameters (Å, º) top
Zn1—O1 | 2.0161 (13) | C13—C14 | 1.516 (2) |
Zn1—O1W | 2.0361 (13) | C4—C3 | 1.404 (3) |
Zn1—O4 | 2.0663 (12) | C4—C5 | 1.434 (3) |
Zn1—N2 | 2.1249 (14) | C14—C15 | 1.510 (2) |
Zn1—N1 | 2.2162 (14) | C14—H14B | 0.9700 |
Zn1—O3 | 2.4441 (15) | C14—H14A | 0.9700 |
Zn1—C16 | 2.5879 (17) | C18—C15i | 1.521 (2) |
O1W—H1WB | 0.77 (3) | C18—H18A | 0.9700 |
O1W—H1WA | 0.85 (3) | C18—H18B | 0.9700 |
O4—C16 | 1.274 (2) | C15—C18i | 1.521 (2) |
O1—C13 | 1.258 (2) | C15—H15A | 0.9700 |
O3—C16 | 1.240 (2) | C15—H15B | 0.9700 |
N2—C10 | 1.329 (2) | C1—C2 | 1.397 (3) |
N2—C11 | 1.356 (2) | C1—H1 | 0.9300 |
N1—C1 | 1.323 (2) | C10—C9 | 1.397 (3) |
N1—C12 | 1.350 (2) | C10—H10 | 0.9300 |
C11—C7 | 1.408 (2) | C6—C5 | 1.339 (3) |
C11—C12 | 1.441 (2) | C6—H6 | 0.9300 |
C16—C17 | 1.506 (2) | C5—H5 | 0.9300 |
O2—C13 | 1.236 (2) | C3—C2 | 1.366 (3) |
C12—C4 | 1.406 (2) | C3—H3 | 0.9300 |
C7—C8 | 1.400 (3) | C8—C9 | 1.360 (3) |
C7—C6 | 1.434 (3) | C8—H8 | 0.9300 |
C17—C18 | 1.528 (2) | C9—H9 | 0.9300 |
C17—H17A | 0.9700 | C2—H2 | 0.9300 |
C17—H17B | 0.9700 | | |
| | | |
O1—Zn1—O1W | 96.49 (6) | C16—C17—H17B | 109.3 |
O1—Zn1—O4 | 101.27 (5) | C18—C17—H17B | 109.3 |
O1W—Zn1—O4 | 101.71 (5) | H17A—C17—H17B | 108.0 |
O1—Zn1—N2 | 89.21 (6) | O2—C13—O1 | 126.37 (17) |
O1W—Zn1—N2 | 106.66 (5) | O2—C13—C14 | 119.28 (15) |
O4—Zn1—N2 | 148.38 (5) | O1—C13—C14 | 114.35 (16) |
O1—Zn1—N1 | 165.55 (6) | C3—C4—C12 | 116.87 (17) |
O1W—Zn1—N1 | 88.77 (5) | C3—C4—C5 | 124.29 (18) |
O4—Zn1—N1 | 90.76 (5) | C12—C4—C5 | 118.84 (19) |
N2—Zn1—N1 | 76.37 (5) | C15—C14—C13 | 117.00 (16) |
O1—Zn1—O3 | 93.97 (6) | C15—C14—H14B | 108.0 |
O1W—Zn1—O3 | 158.19 (5) | C13—C14—H14B | 108.0 |
O4—Zn1—O3 | 57.35 (5) | C15—C14—H14A | 108.0 |
N2—Zn1—O3 | 92.53 (5) | C13—C14—H14A | 108.0 |
N1—Zn1—O3 | 85.75 (5) | H14B—C14—H14A | 107.3 |
O1—Zn1—C16 | 96.77 (6) | C15i—C18—C17 | 114.13 (15) |
O1W—Zn1—C16 | 130.77 (5) | C15i—C18—H18A | 108.7 |
O4—Zn1—C16 | 29.10 (5) | C17—C18—H18A | 108.7 |
N2—Zn1—C16 | 120.70 (5) | C15i—C18—H18B | 108.7 |
N1—Zn1—C16 | 89.84 (5) | C17—C18—H18B | 108.7 |
O3—Zn1—C16 | 28.36 (5) | H18A—C18—H18B | 107.6 |
Zn1—O1W—H1WB | 118.1 (17) | C14—C15—C18i | 111.63 (15) |
Zn1—O1W—H1WA | 113.0 (16) | C14—C15—H15A | 109.3 |
H1WB—O1W—H1WA | 108 (2) | C18i—C15—H15A | 109.3 |
C16—O4—Zn1 | 98.80 (10) | C14—C15—H15B | 109.3 |
C13—O1—Zn1 | 140.64 (13) | C18i—C15—H15B | 109.3 |
C16—O3—Zn1 | 82.27 (11) | H15A—C15—H15B | 108.0 |
C10—N2—C11 | 118.11 (16) | N1—C1—C2 | 122.70 (18) |
C10—N2—Zn1 | 126.04 (13) | N1—C1—H1 | 118.6 |
C11—N2—Zn1 | 115.81 (11) | C2—C1—H1 | 118.6 |
C1—N1—C12 | 118.27 (15) | N2—C10—C9 | 122.6 (2) |
C1—N1—Zn1 | 128.68 (12) | N2—C10—H10 | 118.7 |
C12—N1—Zn1 | 113.04 (11) | C9—C10—H10 | 118.7 |
N2—C11—C7 | 122.69 (17) | C5—C6—C7 | 121.28 (18) |
N2—C11—C12 | 117.39 (14) | C5—C6—H6 | 119.4 |
C7—C11—C12 | 119.91 (16) | C7—C6—H6 | 119.4 |
O3—C16—O4 | 121.11 (16) | C6—C5—C4 | 121.66 (18) |
O3—C16—C17 | 121.21 (16) | C6—C5—H5 | 119.2 |
O4—C16—C17 | 117.67 (15) | C4—C5—H5 | 119.2 |
O3—C16—Zn1 | 69.37 (10) | C2—C3—C4 | 119.69 (17) |
O4—C16—Zn1 | 52.10 (8) | C2—C3—H3 | 120.2 |
C17—C16—Zn1 | 167.53 (12) | C4—C3—H3 | 120.2 |
N1—C12—C4 | 123.15 (17) | C9—C8—C7 | 119.80 (18) |
N1—C12—C11 | 117.31 (14) | C9—C8—H8 | 120.1 |
C4—C12—C11 | 119.54 (16) | C7—C8—H8 | 120.1 |
C8—C7—C11 | 117.27 (18) | C8—C9—C10 | 119.5 (2) |
C8—C7—C6 | 123.99 (18) | C8—C9—H9 | 120.2 |
C11—C7—C6 | 118.74 (19) | C10—C9—H9 | 120.2 |
C16—C17—C18 | 111.58 (14) | C3—C2—C1 | 119.32 (19) |
C16—C17—H17A | 109.3 | C3—C2—H2 | 120.3 |
C18—C17—H17A | 109.3 | C1—C2—H2 | 120.3 |
| | | |
O1—Zn1—O4—C16 | −83.64 (10) | O1—Zn1—C16—O4 | 101.03 (10) |
O1W—Zn1—O4—C16 | 177.21 (9) | O1W—Zn1—C16—O4 | −3.61 (12) |
N2—Zn1—O4—C16 | 23.64 (15) | N2—Zn1—C16—O4 | −165.85 (9) |
N1—Zn1—O4—C16 | 88.30 (10) | N1—Zn1—C16—O4 | −91.85 (10) |
O3—Zn1—O4—C16 | 3.85 (9) | O3—Zn1—C16—O4 | −173.17 (15) |
O1W—Zn1—O1—C13 | 79.1 (2) | O1—Zn1—C16—C17 | 63.7 (5) |
O4—Zn1—O1—C13 | −24.3 (2) | O1W—Zn1—C16—C17 | −40.9 (5) |
N2—Zn1—O1—C13 | −174.2 (2) | O4—Zn1—C16—C17 | −37.3 (5) |
N1—Zn1—O1—C13 | −170.13 (19) | N2—Zn1—C16—C17 | 156.8 (5) |
O3—Zn1—O1—C13 | −81.8 (2) | N1—Zn1—C16—C17 | −129.2 (5) |
C16—Zn1—O1—C13 | −53.4 (2) | O3—Zn1—C16—C17 | 149.5 (6) |
O1—Zn1—O3—C16 | 96.91 (10) | C1—N1—C12—C4 | −0.1 (2) |
O1W—Zn1—O3—C16 | −21.68 (19) | Zn1—N1—C12—C4 | 178.89 (12) |
O4—Zn1—O3—C16 | −3.94 (9) | C1—N1—C12—C11 | 179.96 (15) |
N2—Zn1—O3—C16 | −173.70 (10) | Zn1—N1—C12—C11 | −1.06 (18) |
N1—Zn1—O3—C16 | −97.58 (10) | N2—C11—C12—N1 | −1.0 (2) |
O1—Zn1—N2—C10 | −0.94 (15) | C7—C11—C12—N1 | 179.67 (14) |
O1W—Zn1—N2—C10 | 95.60 (15) | N2—C11—C12—C4 | 179.08 (14) |
O4—Zn1—N2—C10 | −111.46 (16) | C7—C11—C12—C4 | −0.3 (2) |
N1—Zn1—N2—C10 | −179.89 (16) | N2—C11—C7—C8 | 1.3 (3) |
O3—Zn1—N2—C10 | −94.88 (15) | C12—C11—C7—C8 | −179.33 (16) |
C16—Zn1—N2—C10 | −98.36 (15) | N2—C11—C7—C6 | −177.65 (15) |
O1—Zn1—N2—C11 | 176.60 (12) | C12—C11—C7—C6 | 1.7 (2) |
O1W—Zn1—N2—C11 | −86.86 (12) | O3—C16—C17—C18 | 108.49 (18) |
O4—Zn1—N2—C11 | 66.08 (16) | O4—C16—C17—C18 | −70.48 (19) |
N1—Zn1—N2—C11 | −2.34 (11) | Zn1—C16—C17—C18 | −37.8 (6) |
O3—Zn1—N2—C11 | 82.66 (12) | Zn1—O1—C13—O2 | −17.5 (4) |
C16—Zn1—N2—C11 | 79.19 (12) | Zn1—O1—C13—C14 | 162.58 (17) |
O1—Zn1—N1—C1 | 176.4 (2) | N1—C12—C4—C3 | −0.6 (2) |
O1W—Zn1—N1—C1 | −71.88 (15) | C11—C12—C4—C3 | 179.38 (15) |
O4—Zn1—N1—C1 | 29.82 (15) | N1—C12—C4—C5 | 178.80 (15) |
N2—Zn1—N1—C1 | −179.36 (16) | C11—C12—C4—C5 | −1.2 (2) |
O3—Zn1—N1—C1 | 87.00 (15) | O2—C13—C14—C15 | −2.2 (3) |
C16—Zn1—N1—C1 | 58.91 (15) | O1—C13—C14—C15 | 177.71 (17) |
O1—Zn1—N1—C12 | −2.5 (3) | C16—C17—C18—C15i | −62.2 (2) |
O1W—Zn1—N1—C12 | 109.27 (11) | C13—C14—C15—C18i | −175.59 (16) |
O4—Zn1—N1—C12 | −149.03 (11) | C12—N1—C1—C2 | 0.6 (3) |
N2—Zn1—N1—C12 | 1.79 (11) | Zn1—N1—C1—C2 | −178.18 (14) |
O3—Zn1—N1—C12 | −91.85 (11) | C11—N2—C10—C9 | −0.7 (3) |
C16—Zn1—N1—C12 | −119.94 (11) | Zn1—N2—C10—C9 | 176.83 (15) |
C10—N2—C11—C7 | −0.3 (2) | C8—C7—C6—C5 | 179.52 (19) |
Zn1—N2—C11—C7 | −178.05 (12) | C11—C7—C6—C5 | −1.6 (3) |
C10—N2—C11—C12 | −179.64 (15) | C7—C6—C5—C4 | 0.0 (3) |
Zn1—N2—C11—C12 | 2.61 (18) | C3—C4—C5—C6 | −179.27 (19) |
Zn1—O3—C16—O4 | 6.29 (14) | C12—C4—C5—C6 | 1.4 (3) |
Zn1—O3—C16—C17 | −172.64 (14) | C12—C4—C3—C2 | 0.7 (3) |
Zn1—O4—C16—O3 | −7.47 (17) | C5—C4—C3—C2 | −178.62 (19) |
Zn1—O4—C16—C17 | 171.50 (11) | C11—C7—C8—C9 | −1.4 (3) |
O1—Zn1—C16—O3 | −85.80 (10) | C6—C7—C8—C9 | 177.50 (19) |
O1W—Zn1—C16—O3 | 169.56 (9) | C7—C8—C9—C10 | 0.6 (3) |
O4—Zn1—C16—O3 | 173.17 (15) | N2—C10—C9—C8 | 0.5 (3) |
N2—Zn1—C16—O3 | 7.32 (12) | C4—C3—C2—C1 | −0.2 (3) |
N1—Zn1—C16—O3 | 81.32 (10) | N1—C1—C2—C3 | −0.5 (3) |
Symmetry code: (i) −x, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···O1 | 0.93 | 2.49 | 3.030 (3) | 117 |
O1W—H1WB···O4ii | 0.77 (2) | 2.06 (2) | 2.750 (2) | 148 (3) |
O1W—H1WA···O2ii | 0.85 (3) | 1.74 (3) | 2.588 (2) | 173 (3) |
C3—H3···O3iii | 0.93 | 2.52 | 3.402 (3) | 158 |
C9—H9···O3iv | 0.93 | 2.50 | 3.142 (3) | 126 |
Symmetry codes: (ii) −x, −y, −z+1; (iii) −x+1, −y, −z; (iv) −x, −y+1, −z. |