The title compound, [Zn(C7H3FO2)2(C5H6N2)2], is a mononuclear zinc(II) compound. The ZnII atom is coordinated by two N atoms from two 2-aminopyridine ligands and two O atoms from two 2-fluorobenzoate anions in a distorted tetrahedral geometry.
Supporting information
CCDC reference: 251577
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.042
- wR factor = 0.126
- Data-to-parameter ratio = 14.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.37
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for O2
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for O3
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for C11
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C1
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C7
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C9
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C10
PLAT301_ALERT_3_C Main Residue Disorder ......................... 5.00 Perc.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C9 - C10 ... 1.38 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C9 - C14 ... 1.37 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C10 - C11 ... 1.37 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C13 - C14 ... 1.37 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
13 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
12 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 (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
Bis(2-aminopyridine-
κN1)bis(2-fluorobenzoato-
κO)zinc(II)
top
Crystal data top
[Zn(C7H3FO2)2(C5H6N2)2] | F(000) = 1088 |
Mr = 531.81 | Dx = 1.492 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 5568 reflections |
a = 9.126 (2) Å | θ = 2.5–26.7° |
b = 11.102 (2) Å | µ = 1.09 mm−1 |
c = 23.411 (2) Å | T = 293 K |
β = 93.707 (3)° | Block, colourless |
V = 2367.0 (7) Å3 | 0.32 × 0.22 × 0.21 mm |
Z = 4 | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 4894 independent reflections |
Radiation source: fine-focus sealed tube | 3969 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
ω scans | θmax = 26.5°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.721, Tmax = 0.803 | k = −12→13 |
13644 measured reflections | l = −19→29 |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0735P)2 + 0.5892P] where P = (Fo2 + 2Fc2)/3 |
4894 reflections | (Δ/σ)max < 0.001 |
334 parameters | Δρmax = 0.55 e Å−3 |
5 restraints | Δρmin = −0.23 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 | Occ. (<1) |
Zn1 | 0.81247 (3) | 0.92808 (3) | 0.621440 (11) | 0.06543 (14) | |
F1 | 1.0661 (4) | 0.8290 (4) | 0.78092 (14) | 0.1189 (12) | 0.64 |
F2 | 0.7545 (5) | 1.3817 (4) | 0.64719 (19) | 0.1385 (15) | 0.64 |
F1' | 1.3431 (7) | 1.0883 (5) | 0.6658 (3) | 0.122 (2) | 0.36 |
F2' | 0.4915 (10) | 1.1349 (6) | 0.5270 (3) | 0.165 (3) | 0.36 |
O1 | 1.0907 (3) | 1.0317 (2) | 0.63424 (9) | 0.1038 (7) | |
O2 | 0.9617 (2) | 0.9128 (2) | 0.68517 (8) | 0.0837 (6) | |
O3 | 0.7146 (3) | 1.05999 (18) | 0.57707 (10) | 0.0882 (6) | |
O4 | 0.7461 (3) | 1.1321 (3) | 0.66251 (11) | 0.1160 (9) | |
N1 | 0.8969 (2) | 0.81817 (19) | 0.56022 (8) | 0.0628 (5) | |
N2 | 0.8348 (3) | 0.9384 (2) | 0.48184 (9) | 0.0713 (6) | |
H2A | 0.7847 | 0.9835 | 0.5032 | 0.086* | |
H2B | 0.8394 | 0.9550 | 0.4461 | 0.086* | |
N3 | 0.6345 (2) | 0.83271 (19) | 0.64657 (8) | 0.0634 (5) | |
N4 | 0.7488 (3) | 0.7588 (3) | 0.72973 (11) | 0.0985 (9) | |
H4A | 0.8283 | 0.7945 | 0.7214 | 0.118* | |
H4B | 0.7469 | 0.7174 | 0.7607 | 0.118* | |
C1 | 1.0780 (3) | 0.9714 (2) | 0.67709 (10) | 0.0653 (6) | |
C2 | 1.1992 (3) | 0.9647 (2) | 0.72305 (11) | 0.0660 (6) | |
C3 | 1.3290 (4) | 1.0266 (3) | 0.71668 (17) | 0.0941 (10) | |
H3 | 1.3409 | 1.0736 | 0.6844 | 0.113* | 0.64 |
C4 | 1.4446 (4) | 1.0169 (5) | 0.7608 (3) | 0.1264 (17) | |
H4 | 1.5323 | 1.0582 | 0.7576 | 0.152* | |
C5 | 1.4256 (6) | 0.9478 (6) | 0.8069 (3) | 0.134 (2) | |
H5 | 1.5019 | 0.9414 | 0.8350 | 0.161* | |
C6 | 1.3020 (5) | 0.8885 (5) | 0.81357 (17) | 0.1142 (14) | |
H6 | 1.2920 | 0.8423 | 0.8462 | 0.137* | |
C7 | 1.1879 (3) | 0.8954 (3) | 0.77206 (12) | 0.0810 (8) | |
H7 | 1.1018 | 0.8528 | 0.7769 | 0.097* | 0.36 |
C8 | 0.6990 (3) | 1.1422 (2) | 0.61315 (12) | 0.0768 (7) | |
C9 | 0.6101 (3) | 1.2508 (2) | 0.59234 (12) | 0.0701 (7) | |
C10 | 0.4934 (5) | 1.2440 (3) | 0.55218 (16) | 0.1016 (11) | |
H10 | 0.4713 | 1.1701 | 0.5350 | 0.122* | 0.64 |
C11 | 0.4082 (5) | 1.3416 (5) | 0.5364 (2) | 0.1287 (16) | |
H11 | 0.3300 | 1.3329 | 0.5092 | 0.154* | |
C12 | 0.4378 (5) | 1.4505 (5) | 0.5603 (2) | 0.1199 (15) | |
H12 | 0.3776 | 1.5160 | 0.5507 | 0.144* | |
C13 | 0.5550 (5) | 1.4644 (4) | 0.5981 (2) | 0.1104 (13) | |
H13 | 0.5803 | 1.5397 | 0.6130 | 0.132* | |
C14 | 0.6354 (4) | 1.3638 (3) | 0.61381 (15) | 0.0944 (10) | |
H14 | 0.7131 | 1.3734 | 0.6412 | 0.113* | 0.36 |
C15 | 0.9638 (3) | 0.7176 (3) | 0.58155 (13) | 0.0800 (7) | |
H15 | 0.9553 | 0.7003 | 0.6201 | 0.096* | |
C16 | 1.0418 (4) | 0.6408 (3) | 0.55093 (16) | 0.0911 (9) | |
H16 | 1.0855 | 0.5725 | 0.5676 | 0.109* | |
C17 | 1.0544 (4) | 0.6678 (3) | 0.49303 (16) | 0.0886 (9) | |
H17 | 1.1087 | 0.6178 | 0.4706 | 0.106* | |
C18 | 0.9879 (3) | 0.7663 (3) | 0.46983 (12) | 0.0765 (7) | |
H18 | 0.9959 | 0.7842 | 0.4313 | 0.092* | |
C19 | 0.9058 (3) | 0.8423 (2) | 0.50421 (10) | 0.0602 (6) | |
C20 | 0.5122 (3) | 0.8397 (3) | 0.61086 (13) | 0.0760 (7) | |
H20 | 0.5158 | 0.8862 | 0.5779 | 0.091* | |
C21 | 0.3844 (3) | 0.7825 (3) | 0.62045 (16) | 0.0866 (8) | |
H21 | 0.3033 | 0.7882 | 0.5944 | 0.104* | |
C22 | 0.3789 (4) | 0.7156 (3) | 0.67015 (17) | 0.0906 (9) | |
H22 | 0.2929 | 0.6760 | 0.6782 | 0.109* | |
C23 | 0.4985 (4) | 0.7082 (3) | 0.70681 (14) | 0.0830 (8) | |
H23 | 0.4948 | 0.6636 | 0.7403 | 0.100* | |
C24 | 0.6288 (3) | 0.7676 (2) | 0.69464 (11) | 0.0690 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.0777 (2) | 0.0776 (2) | 0.04124 (18) | −0.01504 (14) | 0.00590 (13) | 0.00025 (11) |
F1 | 0.107 (2) | 0.165 (3) | 0.0838 (19) | −0.015 (2) | 0.0008 (16) | 0.045 (2) |
F2 | 0.147 (3) | 0.110 (2) | 0.148 (3) | −0.020 (2) | −0.071 (3) | −0.018 (2) |
F1' | 0.110 (4) | 0.105 (4) | 0.155 (6) | −0.039 (3) | 0.047 (4) | 0.002 (4) |
F2' | 0.201 (8) | 0.134 (6) | 0.149 (7) | −0.037 (6) | −0.076 (6) | −0.003 (5) |
O1 | 0.144 (2) | 0.1077 (16) | 0.0626 (12) | 0.0066 (15) | 0.0285 (13) | 0.0204 (12) |
O2 | 0.0821 (13) | 0.1090 (16) | 0.0585 (11) | −0.0227 (11) | −0.0070 (9) | 0.0061 (10) |
O3 | 0.1266 (18) | 0.0702 (12) | 0.0710 (13) | −0.0092 (11) | 0.0311 (12) | −0.0094 (9) |
O4 | 0.141 (2) | 0.125 (2) | 0.0801 (16) | 0.0363 (18) | −0.0079 (14) | −0.0235 (15) |
N1 | 0.0693 (12) | 0.0696 (12) | 0.0496 (10) | −0.0118 (10) | 0.0047 (9) | −0.0006 (9) |
N2 | 0.0906 (16) | 0.0778 (15) | 0.0465 (11) | −0.0001 (11) | 0.0120 (10) | 0.0003 (9) |
N3 | 0.0732 (12) | 0.0673 (12) | 0.0510 (10) | −0.0073 (10) | 0.0139 (9) | −0.0014 (9) |
N4 | 0.1018 (18) | 0.124 (2) | 0.0700 (15) | −0.0182 (17) | 0.0069 (14) | 0.0356 (16) |
C1 | 0.0812 (17) | 0.0682 (14) | 0.0478 (12) | 0.0027 (13) | 0.0148 (11) | −0.0075 (11) |
C2 | 0.0661 (14) | 0.0692 (15) | 0.0640 (15) | 0.0025 (12) | 0.0132 (11) | −0.0198 (12) |
C3 | 0.0785 (19) | 0.089 (2) | 0.117 (3) | −0.0104 (17) | 0.0225 (19) | −0.031 (2) |
C4 | 0.066 (2) | 0.140 (4) | 0.173 (5) | −0.012 (2) | 0.012 (3) | −0.071 (4) |
C5 | 0.092 (3) | 0.177 (5) | 0.129 (4) | 0.034 (3) | −0.024 (3) | −0.062 (4) |
C6 | 0.097 (3) | 0.166 (4) | 0.078 (2) | 0.032 (3) | −0.0138 (19) | −0.015 (2) |
C7 | 0.0747 (17) | 0.108 (2) | 0.0604 (16) | 0.0087 (16) | 0.0024 (13) | −0.0085 (15) |
C8 | 0.0861 (18) | 0.0776 (18) | 0.0696 (17) | −0.0130 (14) | 0.0277 (14) | −0.0204 (14) |
C9 | 0.0738 (15) | 0.0686 (16) | 0.0704 (15) | −0.0112 (12) | 0.0245 (13) | −0.0142 (12) |
C10 | 0.122 (3) | 0.090 (2) | 0.091 (2) | −0.032 (2) | −0.007 (2) | 0.0010 (19) |
C11 | 0.105 (3) | 0.136 (4) | 0.141 (4) | −0.027 (3) | −0.023 (3) | 0.035 (3) |
C12 | 0.097 (3) | 0.118 (3) | 0.146 (4) | 0.010 (2) | 0.020 (3) | 0.020 (3) |
C13 | 0.127 (3) | 0.073 (2) | 0.134 (3) | 0.010 (2) | 0.033 (3) | −0.022 (2) |
C14 | 0.090 (2) | 0.093 (2) | 0.101 (2) | −0.0063 (18) | 0.0097 (18) | −0.0305 (19) |
C15 | 0.0920 (19) | 0.0808 (19) | 0.0669 (16) | −0.0048 (16) | 0.0014 (14) | 0.0034 (14) |
C16 | 0.089 (2) | 0.081 (2) | 0.104 (2) | 0.0057 (16) | 0.0057 (18) | 0.0028 (18) |
C17 | 0.085 (2) | 0.081 (2) | 0.102 (2) | −0.0041 (16) | 0.0274 (17) | −0.0144 (18) |
C18 | 0.0842 (17) | 0.0798 (18) | 0.0684 (16) | −0.0131 (15) | 0.0265 (13) | −0.0094 (14) |
C19 | 0.0613 (13) | 0.0684 (15) | 0.0518 (12) | −0.0183 (11) | 0.0098 (10) | −0.0068 (11) |
C20 | 0.0833 (18) | 0.0725 (17) | 0.0721 (16) | −0.0089 (14) | 0.0034 (13) | 0.0011 (13) |
C21 | 0.0727 (17) | 0.0793 (19) | 0.108 (2) | −0.0062 (15) | 0.0062 (15) | −0.0070 (17) |
C22 | 0.083 (2) | 0.0727 (18) | 0.120 (3) | −0.0140 (15) | 0.036 (2) | −0.0071 (18) |
C23 | 0.099 (2) | 0.0689 (17) | 0.0851 (19) | −0.0087 (15) | 0.0372 (17) | 0.0052 (14) |
C24 | 0.0827 (17) | 0.0651 (15) | 0.0613 (14) | −0.0019 (13) | 0.0204 (13) | −0.0002 (12) |
Geometric parameters (Å, º) top
Zn1—O2 | 1.962 (2) | C9—C14 | 1.365 (4) |
Zn1—O3 | 1.975 (2) | C9—C10 | 1.377 (4) |
Zn1—N3 | 2.056 (2) | C11—C12 | 1.352 (7) |
Zn1—N1 | 2.069 (2) | C11—C10 | 1.370 (6) |
O1—C1 | 1.217 (3) | C11—H11 | 0.93 |
O2—C1 | 1.269 (3) | C12—C13 | 1.352 (6) |
O3—C8 | 1.258 (3) | C12—H12 | 0.93 |
O4—C8 | 1.212 (4) | C13—C14 | 1.374 (6) |
N1—C19 | 1.346 (3) | C13—H13 | 0.93 |
N1—C15 | 1.352 (4) | C15—C16 | 1.347 (5) |
N2—C19 | 1.337 (3) | C15—H15 | 0.93 |
N2—H2A | 0.86 | C16—C17 | 1.400 (5) |
N2—H2B | 0.86 | C16—H16 | 0.93 |
N3—C24 | 1.341 (3) | C17—C18 | 1.348 (5) |
N3—C20 | 1.353 (4) | C17—H17 | 0.93 |
N4—C24 | 1.329 (4) | C18—C19 | 1.414 (4) |
N4—H4A | 0.86 | C18—H18 | 0.93 |
N4—H4B | 0.86 | C20—C21 | 1.359 (4) |
C1—C2 | 1.495 (4) | C20—H20 | 0.93 |
C2—C3 | 1.386 (4) | C21—C22 | 1.384 (5) |
C2—C7 | 1.391 (4) | C21—H21 | 0.93 |
C4—C5 | 1.344 (8) | C22—C23 | 1.347 (5) |
C4—C3 | 1.432 (6) | C22—H22 | 0.93 |
C4—H4 | 0.93 | C23—C24 | 1.405 (4) |
C5—C6 | 1.324 (8) | C23—H23 | 0.93 |
C5—H5 | 0.93 | F1—C7 | 1.361 (3) |
C6—C7 | 1.379 (5) | F2—C14 | 1.312 (3) |
C6—H6 | 0.93 | C3—H3 | 0.93 |
C8—C9 | 1.516 (3) | C10—H10 | 0.93 |
| | | |
O2—Zn1—O3 | 137.10 (10) | C11—C12—H12 | 120.0 |
O2—Zn1—N3 | 105.08 (9) | C13—C12—H12 | 120.0 |
O3—Zn1—N3 | 101.15 (10) | C12—C13—C14 | 118.0 (4) |
O2—Zn1—N1 | 101.78 (9) | C12—C13—H13 | 121.0 |
O3—Zn1—N1 | 104.43 (8) | C14—C13—H13 | 121.0 |
N3—Zn1—N1 | 103.36 (8) | C16—C15—N1 | 124.6 (3) |
C1—O2—Zn1 | 112.83 (17) | C16—C15—H15 | 117.7 |
C8—O3—Zn1 | 104.6 (2) | N1—C15—H15 | 117.7 |
C19—N1—C15 | 118.0 (2) | C15—C16—C17 | 117.3 (3) |
C19—N1—Zn1 | 127.31 (18) | C15—C16—H16 | 121.4 |
C15—N1—Zn1 | 114.24 (17) | C17—C16—H16 | 121.4 |
C19—N2—H2A | 120.0 | C18—C17—C16 | 120.1 (3) |
C19—N2—H2B | 120.0 | C18—C17—H17 | 120.0 |
H2A—N2—H2B | 120.0 | C16—C17—H17 | 120.0 |
C24—N3—C20 | 118.3 (2) | C17—C18—C19 | 119.7 (3) |
C24—N3—Zn1 | 126.28 (18) | C17—C18—H18 | 120.1 |
C20—N3—Zn1 | 115.39 (17) | C19—C18—H18 | 120.1 |
C24—N4—H4A | 120.0 | N2—C19—N1 | 118.8 (2) |
C24—N4—H4B | 120.0 | N2—C19—C18 | 120.9 (2) |
H4A—N4—H4B | 120.0 | N1—C19—C18 | 120.2 (3) |
O1—C1—O2 | 122.0 (3) | N3—C20—C21 | 123.6 (3) |
O1—C1—C2 | 121.0 (3) | N3—C20—H20 | 118.2 |
O2—C1—C2 | 117.0 (2) | C21—C20—H20 | 118.2 |
C3—C2—C7 | 118.2 (3) | C20—C21—C22 | 117.9 (3) |
C3—C2—C1 | 119.7 (3) | C20—C21—H21 | 121.1 |
C7—C2—C1 | 122.0 (2) | C22—C21—H21 | 121.1 |
C5—C4—C3 | 119.7 (4) | C23—C22—C21 | 119.8 (3) |
C5—C4—H4 | 120.2 | C23—C22—H22 | 120.1 |
C3—C4—H4 | 120.2 | C21—C22—H22 | 120.1 |
C6—C5—C4 | 122.3 (4) | C22—C23—C24 | 120.3 (3) |
C6—C5—H5 | 118.9 | C22—C23—H23 | 119.9 |
C4—C5—H5 | 118.9 | C24—C23—H23 | 119.9 |
C5—C6—C7 | 119.9 (5) | N4—C24—N3 | 118.9 (2) |
C5—C6—H6 | 120.0 | N4—C24—C23 | 121.0 (3) |
C7—C6—H6 | 120.0 | N3—C24—C23 | 120.2 (3) |
O4—C8—O3 | 121.6 (3) | F1—C7—C6 | 116.7 (4) |
O4—C8—C9 | 122.0 (3) | F1—C7—C2 | 122.0 (3) |
O3—C8—C9 | 116.3 (3) | C6—C7—C2 | 121.3 (3) |
O4—C8—Zn1 | 74.24 (19) | F2—C14—C9 | 118.2 (3) |
O3—C8—Zn1 | 47.44 (15) | F2—C14—C13 | 116.3 (4) |
C9—C8—Zn1 | 162.8 (2) | C9—C14—C13 | 125.0 (3) |
C14—C9—C10 | 114.0 (3) | C2—C3—C4 | 118.7 (4) |
C14—C9—C8 | 122.6 (3) | C2—C3—H3 | 120.7 |
C10—C9—C8 | 123.4 (3) | C4—C3—H3 | 120.7 |
C12—C11—C10 | 120.0 (4) | C11—C10—C9 | 122.8 (4) |
C12—C11—H11 | 120.0 | C11—C10—H10 | 118.6 |
C10—C11—H11 | 120.0 | C9—C10—H10 | 118.6 |
C11—C12—C13 | 120.1 (4) | | |
| | | |
O3—Zn1—O2—C1 | −51.6 (3) | C15—C16—C17—C18 | −1.1 (5) |
N3—Zn1—O2—C1 | −177.40 (19) | C16—C17—C18—C19 | 0.2 (5) |
N1—Zn1—O2—C1 | 75.1 (2) | C15—N1—C19—N2 | 177.1 (2) |
O2—Zn1—O3—C8 | −36.6 (3) | Zn1—N1—C19—N2 | −10.8 (3) |
N3—Zn1—O3—C8 | 90.4 (2) | C15—N1—C19—C18 | −2.5 (3) |
N1—Zn1—O3—C8 | −162.48 (18) | Zn1—N1—C19—C18 | 169.68 (18) |
O2—Zn1—N1—C19 | −135.18 (19) | C17—C18—C19—N2 | −177.9 (3) |
O3—Zn1—N1—C19 | 10.5 (2) | C17—C18—C19—N1 | 1.6 (4) |
N3—Zn1—N1—C19 | 116.0 (2) | C24—N3—C20—C21 | −1.3 (4) |
O2—Zn1—N1—C15 | 37.2 (2) | Zn1—N3—C20—C21 | 179.9 (2) |
O3—Zn1—N1—C15 | −177.07 (19) | N3—C20—C21—C22 | 1.4 (5) |
N3—Zn1—N1—C15 | −71.6 (2) | C20—C21—C22—C23 | −0.6 (5) |
O2—Zn1—N3—C24 | −4.3 (2) | C21—C22—C23—C24 | −0.3 (5) |
O3—Zn1—N3—C24 | −150.1 (2) | C20—N3—C24—N4 | 179.2 (3) |
N1—Zn1—N3—C24 | 102.0 (2) | Zn1—N3—C24—N4 | −2.1 (4) |
O2—Zn1—N3—C20 | 174.40 (19) | C20—N3—C24—C23 | 0.4 (4) |
O3—Zn1—N3—C20 | 28.7 (2) | Zn1—N3—C24—C23 | 179.0 (2) |
N1—Zn1—N3—C20 | −79.3 (2) | C22—C23—C24—N4 | −178.4 (3) |
Zn1—O2—C1—O1 | 1.2 (4) | C22—C23—C24—N3 | 0.4 (4) |
Zn1—O2—C1—C2 | −179.48 (17) | C5—C6—C7—F1 | 177.9 (4) |
O1—C1—C2—C3 | −0.8 (4) | C5—C6—C7—C2 | −0.6 (6) |
O2—C1—C2—C3 | 179.9 (3) | C3—C2—C7—F1 | −178.0 (3) |
O1—C1—C2—C7 | −179.2 (3) | C1—C2—C7—F1 | 0.4 (5) |
O2—C1—C2—C7 | 1.5 (4) | C3—C2—C7—C6 | 0.4 (5) |
C3—C4—C5—C6 | −0.8 (7) | C1—C2—C7—C6 | 178.8 (3) |
C4—C5—C6—C7 | 0.9 (7) | C10—C9—C14—F2 | −172.1 (4) |
Zn1—O3—C8—O4 | 3.1 (4) | C8—C9—C14—F2 | 10.5 (5) |
Zn1—O3—C8—C9 | −173.20 (19) | C10—C9—C14—C13 | −0.1 (5) |
O4—C8—C9—C14 | 34.1 (5) | C8—C9—C14—C13 | −177.5 (3) |
O3—C8—C9—C14 | −149.6 (3) | C12—C13—C14—F2 | 175.0 (5) |
O4—C8—C9—C10 | −143.0 (4) | C12—C13—C14—C9 | 2.9 (6) |
O3—C8—C9—C10 | 33.3 (4) | C7—C2—C3—C4 | −0.4 (4) |
C10—C11—C12—C13 | 2.6 (7) | C1—C2—C3—C4 | −178.8 (3) |
C11—C12—C13—C14 | −4.1 (7) | C5—C4—C3—C2 | 0.6 (6) |
C19—N1—C15—C16 | 1.6 (4) | C12—C11—C10—C9 | 0.3 (7) |
Zn1—N1—C15—C16 | −171.6 (3) | C14—C9—C10—C11 | −1.6 (5) |
N1—C15—C16—C17 | 0.2 (5) | C8—C9—C10—C11 | 175.8 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O3 | 0.86 | 2.06 | 2.883 (3) | 159 |
N2—H2B···O1i | 0.86 | 2.03 | 2.863 (3) | 163 |
N4—H4A···F1 | 0.86 | 2.53 | 3.159 (4) | 131 |
N4—H4A···O2 | 0.86 | 2.01 | 2.837 (3) | 160 |
N4—H4B···O4ii | 0.86 | 2.03 | 2.886 (3) | 175 |
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+3/2, y−1/2, −z+3/2. |