Reacting zinc(II) with 2-(2-hydroxyphenyl)benzimidazole, H(hpb), and 2-(4-amino-2-hydroxyphenyl)benzimidazole, H(apb), yields a cocrystalline mixture of Zn(hpb)2 and Zn(apb)2, complexes of the two deprotonated phenolate ligands. The ligands chelate to the ZnII ions in a tetrahedral geometry and are statistically disordered with an occupancy ratio of 0.56 (1):0.44 (1). Ethanol and water molecules also cocrystallize in the crystal structure, with the O atom of the solvent water molecule located on a twofold axis, giving an overall formula [Zn(C13H9.44N2.44O)2]·2C2H6O·0.5H2O. The neutral complexes are connected to one another by intermolecular hydrogen bonding interactions that extend into three-dimensional arrays.
Supporting information
CCDC reference: 282631
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.009 Å
- Disorder in main residue
- R factor = 0.056
- wR factor = 0.140
- Data-to-parameter ratio = 15.8
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D H1W .. H5C .. 1.32 Ang.
Alert level C
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
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2
PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for C50
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C52
PLAT301_ALERT_3_C Main Residue Disorder ......................... 8.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
PLAT417_ALERT_2_C Short Inter D-H..H-D H1W .. H2A .. 2.11 Ang.
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 27.00
From the CIF: _reflns_number_total 5974
Count of symmetry unique reflns 3339
Completeness (_total/calc) 178.92%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 2635
Fraction of Friedel pairs measured 0.789
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
12 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
6 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
2 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXL97.
Bis[2-(benzoimidazol-2-yl)phenolato-
κ2N,
O]zinc(II)–
bis[5-amino-2-(benzoimidazol-2-yl)phenolato-
κ2N,
O]zinc(II)–ethanol–water (0.56/0.44/2/0.5)
top
Crystal data top
[Zn(C13H9.44N2.44O)2]·2C2H6O·0.5H2O | F(000) = 2496 |
Mr = 598.21 | Dx = 1.345 Mg m−3 |
Orthorhombic, Iba2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: I 2 -2c | Cell parameters from 2666 reflections |
a = 32.131 (4) Å | θ = 2.5–20.7° |
b = 9.7172 (13) Å | µ = 0.88 mm−1 |
c = 18.918 (2) Å | T = 293 K |
V = 5906.7 (13) Å3 | Plate, colorless |
Z = 8 | 0.35 × 0.27 × 0.04 mm |
Data collection top
Bruker APEX area-detector diffractometer | 5974 independent reflections |
Radiation source: fine-focus sealed tube | 3932 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
φ and ω scans | θmax = 27.0°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −41→27 |
Tmin = 0.749, Tmax = 0.966 | k = −12→11 |
15485 measured reflections | l = −18→24 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.056 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.140 | w = 1/[σ2(Fo2) + (0.063P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
5974 reflections | Δρmax = 0.51 e Å−3 |
378 parameters | Δρmin = −0.34 e Å−3 |
8 restraints | Absolute structure: Flack (1983), 2640 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.026 (16) |
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) |
C3 | 0.0901 (2) | 0.2171 (7) | 0.3823 (5) | 0.085 (2) | 0.44 |
N5 | 0.0875 (4) | 0.0896 (10) | 0.4110 (7) | 0.086 (4) | 0.44 |
H5A | 0.0673 | 0.0359 | 0.3996 | 0.103* | 0.44 |
H5B | 0.1061 | 0.0624 | 0.4406 | 0.103* | 0.44 |
C3' | 0.0901 (2) | 0.2171 (7) | 0.3823 (5) | 0.085 (2) | 0.56 |
H3' | 0.0900 | 0.1304 | 0.4031 | 0.102* | 0.56 |
C16 | 0.1954 (2) | 1.1134 (6) | 0.5562 (3) | 0.0653 (17) | 0.44 |
N6 | 0.1812 (4) | 1.1839 (10) | 0.6131 (4) | 0.064 (3) | 0.44 |
H6A | 0.1570 | 1.1657 | 0.6302 | 0.077* | 0.44 |
H6B | 0.1963 | 1.2468 | 0.6320 | 0.077* | 0.44 |
C16' | 0.1954 (2) | 1.1134 (6) | 0.5562 (3) | 0.0653 (17) | 0.56 |
H16' | 0.1873 | 1.1668 | 0.5946 | 0.078* | 0.56 |
Zn1 | 0.155582 (15) | 0.72139 (6) | 0.37036 (5) | 0.05353 (18) | |
N1 | 0.11026 (13) | 0.7235 (4) | 0.3005 (2) | 0.0510 (10) | |
N2 | 0.05871 (13) | 0.6430 (5) | 0.2363 (3) | 0.0606 (12) | |
H2A | 0.0401 | 0.5879 | 0.2200 | 0.073* | |
N3 | 0.21105 (12) | 0.7838 (4) | 0.3435 (2) | 0.0493 (10) | |
N4 | 0.27356 (12) | 0.8757 (4) | 0.35384 (19) | 0.0508 (11) | |
H4A | 0.2936 | 0.9247 | 0.3705 | 0.061* | |
O1 | 0.15365 (9) | 0.5252 (4) | 0.3850 (2) | 0.0593 (10) | |
O2 | 0.15289 (11) | 0.8348 (5) | 0.4532 (2) | 0.0710 (11) | |
O5 | −0.03432 (17) | 0.6925 (6) | 0.0618 (3) | 0.1072 (17) | |
H5C | −0.0218 | 0.6335 | 0.0844 | 0.161* | |
O6 | 0.88186 (18) | 0.7011 (6) | 0.0643 (3) | 0.1094 (17) | |
H6C | 0.9067 | 0.6813 | 0.0649 | 0.164* | |
C1 | 0.12161 (13) | 0.4414 (5) | 0.3688 (3) | 0.0539 (11) | |
C2 | 0.1211 (2) | 0.3113 (6) | 0.3979 (3) | 0.0668 (16) | |
H2B | 0.1421 | 0.2861 | 0.4290 | 0.080* | |
C4 | 0.0594 (2) | 0.2547 (7) | 0.3352 (4) | 0.083 (2) | |
H4B | 0.0387 | 0.1919 | 0.3234 | 0.100* | |
C5 | 0.05898 (19) | 0.3794 (7) | 0.3062 (4) | 0.0757 (18) | |
H5D | 0.0377 | 0.4010 | 0.2748 | 0.091* | |
C6 | 0.08922 (15) | 0.4803 (6) | 0.3210 (3) | 0.0535 (13) | |
C7 | 0.08664 (15) | 0.6134 (5) | 0.2876 (3) | 0.0507 (13) | |
C8 | 0.06526 (17) | 0.7768 (6) | 0.2146 (3) | 0.0591 (14) | |
C9 | 0.0471 (2) | 0.8563 (8) | 0.1622 (4) | 0.084 (2) | |
H9A | 0.0259 | 0.8214 | 0.1338 | 0.101* | |
C10 | 0.0613 (2) | 0.9881 (8) | 0.1539 (4) | 0.086 (2) | |
H10A | 0.0491 | 1.0448 | 0.1202 | 0.103* | |
C11 | 0.09336 (19) | 1.0380 (7) | 0.1946 (4) | 0.0783 (18) | |
H11A | 0.1024 | 1.1278 | 0.1875 | 0.094* | |
C12 | 0.11248 (19) | 0.9584 (6) | 0.2457 (4) | 0.0724 (16) | |
H12A | 0.1343 | 0.9923 | 0.2728 | 0.087* | |
C13 | 0.09757 (15) | 0.8257 (6) | 0.2547 (3) | 0.0531 (13) | |
C14 | 0.18016 (16) | 0.9284 (5) | 0.4728 (3) | 0.0502 (12) | |
C15 | 0.16961 (17) | 1.0153 (7) | 0.5292 (3) | 0.0621 (15) | |
H15A | 0.1434 | 1.0054 | 0.5494 | 0.075* | |
C17 | 0.2340 (2) | 1.1314 (7) | 0.5250 (3) | 0.0666 (17) | |
H17A | 0.2521 | 1.1977 | 0.5425 | 0.080* | |
C18 | 0.24547 (17) | 1.0523 (6) | 0.4685 (3) | 0.0613 (14) | |
H18A | 0.2713 | 1.0676 | 0.4477 | 0.074* | |
C19 | 0.21999 (15) | 0.9498 (5) | 0.4412 (2) | 0.0476 (12) | |
C20 | 0.23405 (13) | 0.8695 (5) | 0.3804 (3) | 0.0469 (11) | |
C21 | 0.27585 (16) | 0.7896 (5) | 0.2955 (3) | 0.0513 (12) | |
C22 | 0.30738 (19) | 0.7612 (6) | 0.2485 (3) | 0.0653 (16) | |
H22A | 0.3335 | 0.8019 | 0.2523 | 0.078* | |
C23 | 0.2981 (2) | 0.6687 (7) | 0.1952 (3) | 0.0718 (18) | |
H23A | 0.3187 | 0.6456 | 0.1629 | 0.086* | |
C24 | 0.2593 (2) | 0.6094 (7) | 0.1881 (3) | 0.0730 (18) | |
H24A | 0.2541 | 0.5494 | 0.1508 | 0.088* | |
C25 | 0.22745 (18) | 0.6387 (6) | 0.2366 (3) | 0.0661 (15) | |
H25A | 0.2014 | 0.5976 | 0.2333 | 0.079* | |
C26 | 0.23667 (15) | 0.7311 (5) | 0.2894 (3) | 0.0506 (12) | |
C50 | −0.0210 (4) | 0.6890 (15) | −0.0099 (4) | 0.207 (7) | |
H50A | −0.0321 | 0.6074 | −0.0326 | 0.249* | |
H50B | 0.0091 | 0.6834 | −0.0115 | 0.249* | |
C51 | −0.0349 (5) | 0.8129 (15) | −0.0492 (8) | 0.247 (9) | |
H51A | −0.0229 | 0.8126 | −0.0956 | 0.370* | |
H51B | −0.0262 | 0.8941 | −0.0243 | 0.370* | |
H51C | −0.0647 | 0.8124 | −0.0530 | 0.370* | |
C52 | 0.8576 (3) | 0.5784 (9) | 0.0711 (6) | 0.145 (4) | |
H52A | 0.8509 | 0.5434 | 0.0244 | 0.174* | |
H52B | 0.8318 | 0.5993 | 0.0953 | 0.174* | |
C53 | 0.8807 (4) | 0.4719 (14) | 0.1112 (11) | 0.278 (12) | |
H53A | 0.8642 | 0.3900 | 0.1145 | 0.416* | |
H53B | 0.8867 | 0.5055 | 0.1578 | 0.416* | |
H53C | 0.9064 | 0.4513 | 0.0873 | 0.416* | |
O1W | 0.0000 | 0.5000 | 0.1515 (3) | 0.0608 (13) | |
H1W | 0.005 (2) | 0.5696 (17) | 0.1261 (10) | 0.073* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C3 | 0.082 (4) | 0.073 (4) | 0.100 (7) | −0.007 (3) | 0.012 (4) | 0.016 (4) |
N5 | 0.086 (8) | 0.059 (8) | 0.111 (10) | −0.001 (6) | −0.013 (7) | 0.051 (7) |
C3' | 0.082 (4) | 0.073 (4) | 0.100 (7) | −0.007 (3) | 0.012 (4) | 0.016 (4) |
C16 | 0.085 (5) | 0.058 (4) | 0.053 (4) | 0.002 (3) | −0.001 (3) | −0.003 (3) |
N6 | 0.097 (8) | 0.040 (6) | 0.055 (6) | 0.001 (5) | 0.016 (6) | −0.032 (4) |
C16' | 0.085 (5) | 0.058 (4) | 0.053 (4) | 0.002 (3) | −0.001 (3) | −0.003 (3) |
Zn1 | 0.0408 (3) | 0.0681 (4) | 0.0517 (3) | −0.0049 (3) | −0.0018 (3) | −0.0040 (4) |
N1 | 0.045 (2) | 0.052 (3) | 0.056 (3) | −0.004 (2) | −0.005 (2) | −0.002 (2) |
N2 | 0.042 (2) | 0.066 (3) | 0.074 (3) | −0.011 (2) | −0.016 (2) | 0.005 (2) |
N3 | 0.043 (2) | 0.062 (3) | 0.042 (2) | −0.007 (2) | 0.0001 (17) | −0.0031 (19) |
N4 | 0.045 (2) | 0.064 (3) | 0.044 (3) | −0.0069 (18) | 0.0049 (17) | −0.0012 (19) |
O1 | 0.0437 (17) | 0.076 (2) | 0.058 (3) | 0.0031 (17) | −0.0109 (17) | 0.0045 (19) |
O2 | 0.051 (2) | 0.097 (3) | 0.064 (2) | −0.016 (2) | 0.0118 (19) | −0.023 (2) |
O5 | 0.110 (4) | 0.124 (5) | 0.088 (4) | 0.027 (3) | −0.018 (3) | 0.010 (3) |
O6 | 0.094 (4) | 0.117 (5) | 0.118 (4) | 0.008 (3) | −0.022 (3) | 0.008 (3) |
C1 | 0.046 (2) | 0.063 (3) | 0.052 (3) | 0.003 (2) | 0.006 (3) | 0.000 (3) |
C2 | 0.068 (4) | 0.057 (4) | 0.075 (4) | 0.004 (3) | 0.006 (3) | 0.017 (3) |
C4 | 0.063 (4) | 0.074 (5) | 0.113 (5) | −0.022 (3) | −0.004 (4) | 0.014 (4) |
C5 | 0.059 (4) | 0.067 (4) | 0.101 (5) | −0.009 (3) | −0.011 (3) | 0.010 (4) |
C6 | 0.043 (3) | 0.060 (4) | 0.057 (3) | −0.004 (2) | 0.006 (2) | 0.001 (3) |
C7 | 0.039 (3) | 0.059 (4) | 0.054 (3) | −0.003 (2) | −0.002 (2) | 0.003 (3) |
C8 | 0.051 (3) | 0.061 (3) | 0.065 (4) | 0.002 (3) | −0.007 (3) | 0.008 (3) |
C9 | 0.065 (4) | 0.087 (5) | 0.100 (5) | 0.000 (4) | −0.027 (4) | 0.014 (4) |
C10 | 0.074 (4) | 0.087 (5) | 0.097 (5) | 0.004 (4) | −0.009 (4) | 0.032 (4) |
C11 | 0.072 (4) | 0.065 (4) | 0.098 (5) | 0.000 (3) | −0.004 (4) | 0.020 (4) |
C12 | 0.063 (4) | 0.068 (4) | 0.087 (4) | −0.004 (3) | 0.002 (3) | 0.005 (3) |
C13 | 0.046 (3) | 0.054 (3) | 0.059 (3) | 0.002 (2) | 0.003 (2) | 0.001 (3) |
C14 | 0.051 (3) | 0.058 (3) | 0.042 (3) | 0.009 (2) | −0.001 (2) | −0.001 (2) |
C15 | 0.056 (3) | 0.081 (4) | 0.049 (3) | 0.011 (3) | 0.005 (3) | 0.001 (3) |
C17 | 0.082 (4) | 0.064 (4) | 0.054 (3) | −0.016 (3) | 0.002 (3) | −0.010 (3) |
C18 | 0.057 (3) | 0.073 (4) | 0.054 (3) | −0.012 (3) | 0.006 (3) | −0.001 (3) |
C19 | 0.051 (3) | 0.054 (3) | 0.037 (3) | 0.005 (2) | −0.001 (2) | 0.004 (2) |
C20 | 0.045 (2) | 0.054 (3) | 0.042 (3) | 0.004 (2) | −0.007 (3) | 0.007 (2) |
C21 | 0.050 (3) | 0.056 (3) | 0.048 (3) | 0.004 (2) | 0.006 (2) | 0.001 (3) |
C22 | 0.052 (3) | 0.077 (4) | 0.067 (4) | −0.001 (3) | 0.013 (3) | −0.004 (3) |
C23 | 0.076 (5) | 0.084 (5) | 0.056 (4) | 0.019 (4) | 0.016 (3) | −0.008 (3) |
C24 | 0.082 (5) | 0.080 (5) | 0.057 (4) | 0.006 (4) | 0.002 (3) | −0.015 (3) |
C25 | 0.060 (4) | 0.084 (4) | 0.055 (3) | −0.011 (3) | 0.002 (3) | −0.015 (3) |
C26 | 0.047 (3) | 0.057 (3) | 0.048 (3) | 0.004 (2) | 0.000 (2) | 0.003 (2) |
C50 | 0.170 (13) | 0.326 (19) | 0.126 (10) | 0.096 (13) | 0.043 (9) | 0.065 (11) |
C51 | 0.164 (13) | 0.42 (3) | 0.151 (12) | 0.070 (14) | 0.057 (10) | 0.119 (14) |
C52 | 0.138 (9) | 0.152 (11) | 0.145 (10) | 0.001 (8) | −0.008 (7) | 0.007 (8) |
C53 | 0.191 (13) | 0.175 (15) | 0.47 (3) | −0.043 (11) | −0.118 (19) | 0.154 (19) |
O1W | 0.053 (3) | 0.065 (4) | 0.064 (3) | −0.011 (3) | 0.000 | 0.000 |
Geometric parameters (Å, º) top
C3—N5 | 1.355 (8) | C9—C10 | 1.369 (10) |
C3—C4 | 1.379 (10) | C9—H9A | 0.9300 |
C3—C2 | 1.384 (9) | C10—C11 | 1.375 (9) |
N5—H5A | 0.8600 | C10—H10A | 0.9300 |
N5—H5B | 0.8600 | C11—C12 | 1.383 (8) |
C16—N6 | 1.354 (8) | C11—H11A | 0.9300 |
C16—C15 | 1.363 (8) | C12—C13 | 1.386 (8) |
C16—C17 | 1.383 (9) | C12—H12A | 0.9300 |
N6—H6A | 0.8600 | C14—C15 | 1.403 (7) |
N6—H6B | 0.8600 | C14—C19 | 1.427 (7) |
Zn1—O2 | 1.918 (4) | C15—H15A | 0.9300 |
Zn1—O1 | 1.927 (4) | C17—C18 | 1.367 (8) |
Zn1—N3 | 1.950 (4) | C17—H17A | 0.9300 |
Zn1—N1 | 1.966 (4) | C18—C19 | 1.390 (7) |
N1—C7 | 1.335 (6) | C18—H18A | 0.9300 |
N1—C13 | 1.380 (7) | C19—C20 | 1.461 (7) |
N2—C7 | 1.353 (6) | C21—C22 | 1.377 (7) |
N2—C8 | 1.379 (7) | C21—C26 | 1.387 (7) |
N2—H2A | 0.8600 | C22—C23 | 1.384 (8) |
N3—C20 | 1.314 (6) | C22—H22A | 0.9300 |
N3—C26 | 1.410 (6) | C23—C24 | 1.380 (9) |
N4—C20 | 1.367 (6) | C23—H23A | 0.9300 |
N4—C21 | 1.386 (6) | C24—C25 | 1.404 (9) |
N4—H4A | 0.8600 | C24—H24A | 0.9300 |
O1—C1 | 1.348 (6) | C25—C26 | 1.374 (8) |
O2—C14 | 1.316 (7) | C25—H25A | 0.9300 |
O5—C50 | 1.424 (5) | C50—C51 | 1.48 (2) |
O5—H5C | 0.8200 | C50—H50A | 0.9700 |
O6—C52 | 1.430 (11) | C50—H50B | 0.9700 |
O6—H6C | 0.8200 | C51—H51A | 0.9600 |
C1—C2 | 1.380 (7) | C51—H51B | 0.9600 |
C1—C6 | 1.430 (7) | C51—H51C | 0.9600 |
C2—H2B | 0.9300 | C52—C53 | 1.482 (18) |
C4—C5 | 1.330 (8) | C52—H52A | 0.9700 |
C4—H4B | 0.9300 | C52—H52B | 0.9700 |
C5—C6 | 1.408 (8) | C53—H53A | 0.9600 |
C5—H5D | 0.9300 | C53—H53B | 0.9600 |
C6—C7 | 1.441 (7) | C53—H53C | 0.9600 |
C8—C13 | 1.371 (7) | O1W—H1W | 0.844 (10) |
C8—C9 | 1.387 (9) | | |
| | | |
N5—C3—C4 | 117.2 (8) | C11—C12—H12A | 121.5 |
N5—C3—C2 | 124.2 (9) | C13—C12—H12A | 121.5 |
C4—C3—C2 | 118.5 (6) | C8—C13—N1 | 108.8 (5) |
C3—N5—H5A | 120.0 | C8—C13—C12 | 121.1 (5) |
C3—N5—H5B | 120.0 | N1—C13—C12 | 130.1 (5) |
H5A—N5—H5B | 120.0 | O2—C14—C15 | 118.0 (5) |
N6—C16—C15 | 116.5 (7) | O2—C14—C19 | 125.4 (5) |
N6—C16—C17 | 125.2 (8) | C15—C14—C19 | 116.6 (5) |
C15—C16—C17 | 118.2 (5) | C16—C15—C14 | 124.0 (5) |
C16—N6—H6A | 120.0 | C16—C15—H15A | 118.0 |
C16—N6—H6B | 120.0 | C14—C15—H15A | 118.0 |
H6A—N6—H6B | 120.0 | C18—C17—C16 | 120.3 (6) |
O2—Zn1—O1 | 116.74 (18) | C18—C17—H17A | 119.9 |
O2—Zn1—N3 | 94.33 (16) | C16—C17—H17A | 119.9 |
O1—Zn1—N3 | 111.99 (16) | C17—C18—C19 | 122.4 (5) |
O2—Zn1—N1 | 120.64 (18) | C17—C18—H18A | 118.8 |
O1—Zn1—N1 | 94.74 (16) | C19—C18—H18A | 118.8 |
N3—Zn1—N1 | 119.91 (17) | C18—C19—C14 | 118.4 (5) |
C7—N1—C13 | 107.1 (4) | C18—C19—C20 | 119.6 (4) |
C7—N1—Zn1 | 122.4 (4) | C14—C19—C20 | 121.9 (5) |
C13—N1—Zn1 | 130.4 (4) | N3—C20—N4 | 110.8 (4) |
C7—N2—C8 | 108.2 (4) | N3—C20—C19 | 125.6 (4) |
C7—N2—H2A | 125.9 | N4—C20—C19 | 123.6 (4) |
C8—N2—H2A | 125.9 | C22—C21—N4 | 132.4 (5) |
C20—N3—C26 | 106.7 (4) | C22—C21—C26 | 122.1 (5) |
C20—N3—Zn1 | 124.9 (3) | N4—C21—C26 | 105.4 (4) |
C26—N3—Zn1 | 127.6 (3) | C21—C22—C23 | 116.2 (5) |
C20—N4—C21 | 108.4 (4) | C21—C22—H22A | 121.9 |
C20—N4—H4A | 125.8 | C23—C22—H22A | 121.9 |
C21—N4—H4A | 125.8 | C24—C23—C22 | 122.5 (6) |
C1—O1—Zn1 | 126.2 (3) | C24—C23—H23A | 118.7 |
C14—O2—Zn1 | 126.6 (3) | C22—C23—H23A | 118.7 |
C50—O5—H5C | 109.5 | C23—C24—C25 | 120.6 (6) |
C52—O6—H6C | 109.5 | C23—C24—H24A | 119.7 |
O1—C1—C2 | 118.2 (5) | C25—C24—H24A | 119.7 |
O1—C1—C6 | 122.7 (4) | C26—C25—C24 | 116.8 (5) |
C2—C1—C6 | 119.1 (5) | C26—C25—H25A | 121.6 |
C1—C2—C3 | 122.0 (6) | C24—C25—H25A | 121.6 |
C1—C2—H2B | 119.0 | C25—C26—C21 | 121.7 (5) |
C3—C2—H2B | 119.0 | C25—C26—N3 | 129.7 (5) |
C5—C4—C3 | 121.0 (6) | C21—C26—N3 | 108.6 (4) |
C5—C4—H4B | 119.5 | O5—C50—C51 | 111.5 (9) |
C3—C4—H4B | 119.5 | O5—C50—H50A | 109.3 |
C4—C5—C6 | 123.1 (6) | C51—C50—H50A | 109.3 |
C4—C5—H5D | 118.5 | O5—C50—H50B | 109.3 |
C6—C5—H5D | 118.5 | C51—C50—H50B | 109.3 |
C5—C6—C1 | 116.3 (5) | H50A—C50—H50B | 108.0 |
C5—C6—C7 | 119.9 (5) | C50—C51—H51A | 109.5 |
C1—C6—C7 | 123.8 (4) | C50—C51—H51B | 109.5 |
N1—C7—N2 | 109.8 (4) | H51A—C51—H51B | 109.5 |
N1—C7—C6 | 127.3 (5) | C50—C51—H51C | 109.5 |
N2—C7—C6 | 122.9 (5) | H51A—C51—H51C | 109.5 |
C13—C8—N2 | 106.1 (5) | H51B—C51—H51C | 109.5 |
C13—C8—C9 | 121.5 (6) | O6—C52—C53 | 110.8 (8) |
N2—C8—C9 | 132.3 (6) | O6—C52—H52A | 109.5 |
C10—C9—C8 | 117.6 (6) | C53—C52—H52A | 109.5 |
C10—C9—H9A | 121.2 | O6—C52—H52B | 109.5 |
C8—C9—H9A | 121.2 | C53—C52—H52B | 109.5 |
C9—C10—C11 | 121.1 (6) | H52A—C52—H52B | 108.1 |
C9—C10—H10A | 119.5 | C52—C53—H53A | 109.5 |
C11—C10—H10A | 119.5 | C52—C53—H53B | 109.5 |
C10—C11—C12 | 121.8 (6) | H53A—C53—H53B | 109.5 |
C10—C11—H11A | 119.1 | C52—C53—H53C | 109.5 |
C12—C11—H11A | 119.1 | H53A—C53—H53C | 109.5 |
C11—C12—C13 | 116.9 (6) | H53B—C53—H53C | 109.5 |
| | | |
O2—Zn1—N1—C7 | −115.4 (4) | C9—C8—C13—N1 | −178.0 (6) |
O1—Zn1—N1—C7 | 9.6 (4) | N2—C8—C13—C12 | 179.4 (5) |
N3—Zn1—N1—C7 | 128.4 (4) | C9—C8—C13—C12 | 1.9 (9) |
O2—Zn1—N1—C13 | 68.1 (5) | C7—N1—C13—C8 | 1.2 (6) |
O1—Zn1—N1—C13 | −166.8 (4) | Zn1—N1—C13—C8 | 178.0 (4) |
N3—Zn1—N1—C13 | −48.1 (5) | C7—N1—C13—C12 | −178.7 (6) |
O2—Zn1—N3—C20 | 3.3 (4) | Zn1—N1—C13—C12 | −1.8 (8) |
O1—Zn1—N3—C20 | −117.8 (4) | C11—C12—C13—C8 | −0.2 (8) |
N1—Zn1—N3—C20 | 132.6 (4) | C11—C12—C13—N1 | 179.7 (6) |
O2—Zn1—N3—C26 | 171.9 (4) | Zn1—O2—C14—C15 | 170.4 (4) |
O1—Zn1—N3—C26 | 50.8 (4) | Zn1—O2—C14—C19 | −9.5 (8) |
N1—Zn1—N3—C26 | −58.8 (5) | N6—C16—C15—C14 | −176.8 (7) |
O2—Zn1—O1—C1 | 108.8 (4) | C17—C16—C15—C14 | 1.9 (9) |
N3—Zn1—O1—C1 | −144.0 (4) | O2—C14—C15—C16 | 177.8 (6) |
N1—Zn1—O1—C1 | −19.1 (4) | C19—C14—C15—C16 | −2.3 (8) |
O1—Zn1—O2—C14 | 123.6 (4) | N6—C16—C17—C18 | 178.6 (7) |
N3—Zn1—O2—C14 | 6.3 (5) | C15—C16—C17—C18 | 0.0 (10) |
N1—Zn1—O2—C14 | −122.5 (4) | C16—C17—C18—C19 | −1.5 (10) |
Zn1—O1—C1—C2 | −164.4 (4) | C17—C18—C19—C14 | 1.0 (8) |
Zn1—O1—C1—C6 | 17.9 (7) | C17—C18—C19—C20 | 179.6 (5) |
O1—C1—C2—C3 | −177.8 (6) | O2—C14—C19—C18 | −179.3 (5) |
C6—C1—C2—C3 | 0.0 (9) | C15—C14—C19—C18 | 0.8 (7) |
N5—C3—C2—C1 | −178.1 (9) | O2—C14—C19—C20 | 2.1 (8) |
C4—C3—C2—C1 | 1.1 (11) | C15—C14—C19—C20 | −177.7 (4) |
N5—C3—C4—C5 | 178.0 (9) | C26—N3—C20—N4 | −0.3 (6) |
C2—C3—C4—C5 | −1.2 (12) | Zn1—N3—C20—N4 | 170.2 (3) |
C3—C4—C5—C6 | 0.2 (12) | C26—N3—C20—C19 | 178.9 (4) |
C4—C5—C6—C1 | 0.9 (9) | Zn1—N3—C20—C19 | −10.5 (7) |
C4—C5—C6—C7 | −179.9 (6) | C21—N4—C20—N3 | 0.8 (6) |
O1—C1—C6—C5 | 176.7 (5) | C21—N4—C20—C19 | −178.5 (4) |
C2—C1—C6—C5 | −1.0 (8) | C18—C19—C20—N3 | −169.9 (5) |
O1—C1—C6—C7 | −2.5 (8) | C14—C19—C20—N3 | 8.6 (8) |
C2—C1—C6—C7 | 179.8 (5) | C18—C19—C20—N4 | 9.2 (8) |
C13—N1—C7—N2 | −1.4 (6) | C14—C19—C20—N4 | −172.2 (4) |
Zn1—N1—C7—N2 | −178.6 (3) | C20—N4—C21—C22 | 177.5 (6) |
C13—N1—C7—C6 | 178.1 (5) | C20—N4—C21—C26 | −0.9 (5) |
Zn1—N1—C7—C6 | 0.9 (7) | N4—C21—C22—C23 | −179.3 (6) |
C8—N2—C7—N1 | 1.2 (6) | C26—C21—C22—C23 | −1.2 (8) |
C8—N2—C7—C6 | −178.4 (5) | C21—C22—C23—C24 | 1.2 (10) |
C5—C6—C7—N1 | 173.3 (5) | C22—C23—C24—C25 | −1.6 (11) |
C1—C6—C7—N1 | −7.5 (8) | C23—C24—C25—C26 | 1.8 (10) |
C5—C6—C7—N2 | −7.2 (8) | C24—C25—C26—C21 | −1.8 (9) |
C1—C6—C7—N2 | 172.0 (5) | C24—C25—C26—N3 | 177.5 (5) |
C7—N2—C8—C13 | −0.4 (6) | C22—C21—C26—C25 | 1.5 (9) |
C7—N2—C8—C9 | 176.7 (7) | N4—C21—C26—C25 | −179.9 (5) |
C13—C8—C9—C10 | −2.8 (10) | C22—C21—C26—N3 | −177.9 (5) |
N2—C8—C9—C10 | −179.5 (6) | N4—C21—C26—N3 | 0.7 (5) |
C8—C9—C10—C11 | 2.0 (11) | C20—N3—C26—C25 | −179.6 (6) |
C9—C10—C11—C12 | −0.4 (11) | Zn1—N3—C26—C25 | 10.2 (8) |
C10—C11—C12—C13 | −0.6 (9) | C20—N3—C26—C21 | −0.3 (6) |
N2—C8—C13—N1 | −0.5 (6) | Zn1—N3—C26—C21 | −170.5 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1W | 0.86 | 2.02 | 2.839 (5) | 160 |
O1W—H1W···O5 | 0.84 (1) | 2.12 (5) | 2.755 (6) | 132 (6) |
N4—H4A···O1i | 0.86 | 1.98 | 2.816 (5) | 165 |
O5—H5C···O1W | 0.82 | 1.95 | 2.755 (6) | 169 |
O6—H6C···O5ii | 0.82 | 1.90 | 2.695 (8) | 163 |
Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) x+1, y, z. |