In the title compound, [Zn(C7H5O2)(C30H28BN6)], the Zn atom is coordinated by three N atoms of the tridentate pyrazolyl groups and the carboxylate O atoms of the benzoate ligand in an isobidentate manner due to a short-range interaction between the Zn atom and the carbonyl O atom [2.593 (2) Å], giving a distorted trigonal–bipyrimidal environment.
Supporting information
CCDC reference: 621558
Key indicators
- Single-crystal X-ray study
- T = 571 K
- Mean (C-C) = 0.005 Å
- R factor = 0.041
- wR factor = 0.104
- Data-to-parameter ratio = 16.2
checkCIF/PLATON results
No syntax errors found
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.110
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.84 Ratio
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C34
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C32
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 1
Alert level G
FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and _chemical_formula_moiety. This is
usually due to the moiety formula being in the wrong format.
Atom count from _chemical_formula_sum: C37 H33 B1 N6 O2 Zn1
Atom count from _chemical_formula_moiety:C37 H32 B1 N6 O1 Zn1
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
2 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
3 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Benzoato[hydridotris(3,5-methylphenylpyrazolyl)borato-
κ3N,
N',
N'']zinc(II)
top
Crystal data top
[Zn(C7H5O2)(C30H28BN6)] | F(000) = 1392 |
Mr = 669.87 | Dx = 1.372 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 19653 reflections |
a = 10.147 (2) Å | θ = 1.7–27.8° |
b = 23.561 (5) Å | µ = 0.80 mm−1 |
c = 13.776 (3) Å | T = 571 K |
β = 100.09 (3)° | Prism, green |
V = 3242.4 (11) Å3 | 0.20 × 0.20 × 0.20 mm |
Z = 4 | |
Data collection top
Bruker 1K CCD diffractometer | 7014 independent reflections |
Radiation source: fine-focus sealed tube | 3841 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.110 |
Detector resolution: 83.66 pixels mm-1 | θmax = 27.0°, θmin = 1.7° |
φ and ω scans | h = −12→12 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −30→30 |
Tmin = 0.856, Tmax = 0.856 | l = −17→17 |
69871 measured reflections | |
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)] = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.104 | w = 1/[σ2(Fo2) + (0.0308P)2 + 2.4383P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
7014 reflections | Δρmax = 0.22 e Å−3 |
432 parameters | Δρmin = −0.42 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0020 (2) |
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 | |
Zn | 0.21168 (3) | 0.37394 (2) | 0.34738 (3) | 0.03957 (13) | |
N1 | 0.2196 (2) | 0.31063 (11) | 0.44808 (17) | 0.0409 (6) | |
N2 | 0.3163 (2) | 0.32156 (11) | 0.52889 (17) | 0.0411 (6) | |
N3 | 0.2634 (2) | 0.44022 (11) | 0.44140 (18) | 0.0413 (6) | |
N4 | 0.3658 (2) | 0.42576 (11) | 0.51725 (18) | 0.0431 (6) | |
N5 | 0.4114 (2) | 0.36146 (10) | 0.33572 (17) | 0.0400 (6) | |
N6 | 0.4868 (2) | 0.35450 (10) | 0.42779 (18) | 0.0399 (6) | |
O1 | 0.0942 (2) | 0.38152 (10) | 0.22263 (15) | 0.0524 (6) | |
O2 | −0.0434 (2) | 0.39215 (11) | 0.32829 (18) | 0.0635 (7) | |
C1 | 0.3809 (4) | 0.29232 (16) | 0.7050 (2) | 0.0624 (10) | |
H1A | 0.4720 | 0.2833 | 0.7006 | 0.094* | |
H1B | 0.3487 | 0.2660 | 0.7487 | 0.094* | |
H1C | 0.3764 | 0.3302 | 0.7298 | 0.094* | |
C2 | 0.2961 (3) | 0.28826 (14) | 0.6048 (2) | 0.0464 (8) | |
C3 | 0.1875 (3) | 0.25472 (14) | 0.5724 (2) | 0.0476 (8) | |
H3 | 0.1511 | 0.2274 | 0.6087 | 0.057* | |
C4 | 0.1420 (3) | 0.26934 (13) | 0.4745 (2) | 0.0409 (8) | |
C5 | 0.0295 (3) | 0.24481 (13) | 0.4057 (2) | 0.0434 (8) | |
C6 | −0.0711 (4) | 0.21580 (16) | 0.4397 (3) | 0.0660 (11) | |
H6 | −0.0674 | 0.2118 | 0.5073 | 0.079* | |
C7 | −0.1770 (4) | 0.19250 (18) | 0.3758 (3) | 0.0763 (12) | |
H7 | −0.2440 | 0.1733 | 0.4007 | 0.092* | |
C8 | −0.1842 (4) | 0.19746 (17) | 0.2766 (3) | 0.0722 (12) | |
H8 | −0.2565 | 0.1822 | 0.2337 | 0.087* | |
C9 | −0.0850 (4) | 0.22491 (18) | 0.2405 (3) | 0.0736 (12) | |
H9 | −0.0884 | 0.2277 | 0.1728 | 0.088* | |
C10 | 0.0208 (3) | 0.24866 (15) | 0.3047 (2) | 0.0571 (9) | |
H10 | 0.0876 | 0.2676 | 0.2793 | 0.069* | |
C11 | 0.4949 (4) | 0.46832 (16) | 0.6717 (3) | 0.0667 (11) | |
H11A | 0.4689 | 0.4423 | 0.7185 | 0.100* | |
H11B | 0.5057 | 0.5056 | 0.7002 | 0.100* | |
H11C | 0.5780 | 0.4561 | 0.6543 | 0.100* | |
C12 | 0.3889 (3) | 0.46982 (14) | 0.5811 (2) | 0.0478 (8) | |
C13 | 0.3020 (3) | 0.51236 (14) | 0.5462 (2) | 0.0517 (9) | |
H13 | 0.2956 | 0.5477 | 0.5751 | 0.062* | |
C14 | 0.2250 (3) | 0.49290 (13) | 0.4593 (2) | 0.0430 (8) | |
C15 | 0.1200 (3) | 0.52422 (13) | 0.3930 (2) | 0.0441 (8) | |
C16 | 0.0376 (3) | 0.56105 (14) | 0.4346 (3) | 0.0556 (9) | |
H16 | 0.0481 | 0.5645 | 0.5028 | 0.067* | |
C17 | −0.0590 (4) | 0.59219 (17) | 0.3753 (4) | 0.0701 (11) | |
H17 | −0.1134 | 0.6167 | 0.4035 | 0.084* | |
C18 | −0.0756 (4) | 0.58741 (18) | 0.2749 (4) | 0.0779 (13) | |
H18 | −0.1412 | 0.6086 | 0.2350 | 0.093* | |
C19 | 0.0045 (4) | 0.55135 (17) | 0.2332 (3) | 0.0676 (11) | |
H19 | −0.0077 | 0.5479 | 0.1649 | 0.081* | |
C20 | 0.1033 (3) | 0.52005 (15) | 0.2915 (3) | 0.0556 (9) | |
H20 | 0.1585 | 0.4963 | 0.2625 | 0.067* | |
C21 | 0.7190 (3) | 0.32762 (16) | 0.5077 (3) | 0.0597 (10) | |
H21A | 0.7248 | 0.3593 | 0.5521 | 0.090* | |
H21B | 0.8034 | 0.3226 | 0.4863 | 0.090* | |
H21C | 0.6977 | 0.2939 | 0.5409 | 0.090* | |
C22 | 0.6124 (3) | 0.33851 (13) | 0.4205 (2) | 0.0430 (8) | |
C23 | 0.6193 (3) | 0.33556 (13) | 0.3225 (2) | 0.0464 (8) | |
H23 | 0.6939 | 0.3257 | 0.2954 | 0.056* | |
C24 | 0.4931 (3) | 0.35017 (13) | 0.2706 (2) | 0.0396 (7) | |
C25 | 0.4494 (3) | 0.35318 (13) | 0.1637 (2) | 0.0427 (8) | |
C26 | 0.5172 (4) | 0.32175 (16) | 0.1021 (3) | 0.0595 (10) | |
H26 | 0.5901 | 0.2996 | 0.1294 | 0.071* | |
C27 | 0.4773 (4) | 0.3232 (2) | 0.0018 (3) | 0.0784 (13) | |
H27 | 0.5230 | 0.3018 | −0.0383 | 0.094* | |
C28 | 0.3710 (5) | 0.3559 (2) | −0.0399 (3) | 0.0838 (14) | |
H28 | 0.3438 | 0.3563 | −0.1080 | 0.101* | |
C29 | 0.3046 (4) | 0.38819 (18) | 0.0191 (3) | 0.0688 (11) | |
H29 | 0.2331 | 0.4109 | −0.0090 | 0.083* | |
C30 | 0.3441 (3) | 0.38690 (14) | 0.1204 (2) | 0.0505 (9) | |
H30 | 0.2991 | 0.4091 | 0.1599 | 0.061* | |
C31 | −0.0201 (3) | 0.39527 (14) | 0.2441 (3) | 0.0465 (8) | |
C32 | −0.1228 (3) | 0.41719 (14) | 0.1613 (2) | 0.0455 (8) | |
C33 | −0.0993 (4) | 0.41836 (19) | 0.0668 (3) | 0.0781 (13) | |
H33 | −0.0194 | 0.4040 | 0.0525 | 0.094* | |
C34 | −0.1942 (5) | 0.4409 (2) | −0.0079 (3) | 0.0989 (16) | |
H34 | −0.1781 | 0.4415 | −0.0723 | 0.119* | |
C35 | −0.3108 (4) | 0.4620 (2) | 0.0127 (4) | 0.0879 (14) | |
H35 | −0.3744 | 0.4771 | −0.0375 | 0.105* | |
C36 | −0.3340 (4) | 0.46117 (19) | 0.1055 (4) | 0.0855 (14) | |
H36 | −0.4138 | 0.4758 | 0.1194 | 0.103* | |
C37 | −0.2408 (3) | 0.43883 (16) | 0.1806 (3) | 0.0663 (11) | |
H37 | −0.2581 | 0.4384 | 0.2447 | 0.080* | |
B | 0.4267 (3) | 0.36598 (16) | 0.5221 (3) | 0.0415 (9) | |
BH | 0.507 (2) | 0.3617 (10) | 0.5870 (18) | 0.031 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn | 0.0374 (2) | 0.0443 (2) | 0.0348 (2) | 0.00498 (18) | 0.00021 (14) | −0.00047 (19) |
N1 | 0.0411 (15) | 0.0457 (17) | 0.0340 (15) | 0.0041 (13) | 0.0008 (12) | −0.0012 (12) |
N2 | 0.0464 (15) | 0.0433 (16) | 0.0314 (14) | 0.0056 (13) | 0.0010 (12) | −0.0003 (12) |
N3 | 0.0392 (14) | 0.0426 (17) | 0.0408 (15) | 0.0053 (12) | 0.0032 (12) | −0.0021 (13) |
N4 | 0.0430 (15) | 0.0433 (17) | 0.0401 (15) | 0.0013 (13) | −0.0005 (12) | −0.0054 (13) |
N5 | 0.0390 (14) | 0.0475 (17) | 0.0314 (14) | 0.0061 (12) | 0.0004 (12) | −0.0024 (12) |
N6 | 0.0350 (14) | 0.0444 (16) | 0.0377 (15) | 0.0054 (11) | −0.0008 (12) | −0.0020 (12) |
O1 | 0.0404 (12) | 0.0680 (16) | 0.0453 (13) | 0.0103 (12) | −0.0019 (10) | 0.0028 (12) |
O2 | 0.0666 (16) | 0.0759 (19) | 0.0462 (15) | 0.0090 (13) | 0.0053 (13) | 0.0051 (13) |
C1 | 0.085 (3) | 0.061 (2) | 0.037 (2) | 0.008 (2) | −0.0010 (19) | 0.0036 (18) |
C2 | 0.055 (2) | 0.049 (2) | 0.0341 (18) | 0.0151 (17) | 0.0072 (16) | 0.0025 (16) |
C3 | 0.057 (2) | 0.046 (2) | 0.041 (2) | 0.0052 (18) | 0.0116 (16) | 0.0049 (17) |
C4 | 0.0428 (18) | 0.041 (2) | 0.0401 (19) | 0.0070 (15) | 0.0112 (15) | 0.0001 (15) |
C5 | 0.0440 (19) | 0.040 (2) | 0.047 (2) | 0.0062 (15) | 0.0108 (16) | −0.0004 (16) |
C6 | 0.072 (3) | 0.075 (3) | 0.054 (2) | −0.012 (2) | 0.022 (2) | −0.006 (2) |
C7 | 0.059 (3) | 0.086 (3) | 0.088 (3) | −0.022 (2) | 0.025 (2) | −0.011 (3) |
C8 | 0.058 (3) | 0.075 (3) | 0.079 (3) | −0.007 (2) | −0.001 (2) | −0.015 (2) |
C9 | 0.075 (3) | 0.086 (3) | 0.054 (2) | −0.018 (2) | −0.004 (2) | −0.003 (2) |
C10 | 0.060 (2) | 0.063 (2) | 0.047 (2) | −0.0174 (19) | 0.0061 (18) | −0.0020 (19) |
C11 | 0.072 (3) | 0.070 (3) | 0.053 (2) | −0.011 (2) | −0.0050 (19) | −0.014 (2) |
C12 | 0.0481 (19) | 0.048 (2) | 0.046 (2) | −0.0084 (17) | 0.0070 (16) | −0.0108 (17) |
C13 | 0.067 (2) | 0.036 (2) | 0.053 (2) | −0.0011 (18) | 0.0145 (18) | −0.0086 (17) |
C14 | 0.0480 (19) | 0.038 (2) | 0.046 (2) | −0.0002 (16) | 0.0171 (16) | −0.0021 (16) |
C15 | 0.0460 (19) | 0.0330 (19) | 0.056 (2) | 0.0027 (15) | 0.0163 (16) | 0.0008 (16) |
C16 | 0.060 (2) | 0.048 (2) | 0.065 (2) | 0.0039 (18) | 0.0252 (19) | −0.0001 (19) |
C17 | 0.059 (2) | 0.057 (3) | 0.099 (3) | 0.020 (2) | 0.026 (2) | 0.007 (2) |
C18 | 0.060 (3) | 0.069 (3) | 0.102 (4) | 0.020 (2) | 0.007 (3) | 0.025 (3) |
C19 | 0.068 (3) | 0.069 (3) | 0.062 (3) | 0.008 (2) | 0.004 (2) | 0.014 (2) |
C20 | 0.057 (2) | 0.052 (2) | 0.060 (2) | 0.0104 (18) | 0.0141 (18) | 0.0045 (19) |
C21 | 0.0402 (19) | 0.068 (3) | 0.066 (2) | 0.0099 (18) | −0.0054 (17) | 0.003 (2) |
C22 | 0.0351 (17) | 0.0364 (19) | 0.055 (2) | 0.0032 (14) | −0.0002 (15) | 0.0005 (16) |
C23 | 0.0379 (18) | 0.048 (2) | 0.054 (2) | 0.0054 (15) | 0.0121 (16) | −0.0005 (17) |
C24 | 0.0404 (18) | 0.0362 (18) | 0.0433 (19) | 0.0015 (14) | 0.0105 (15) | −0.0007 (15) |
C25 | 0.0427 (18) | 0.045 (2) | 0.0422 (19) | −0.0036 (15) | 0.0119 (16) | −0.0037 (15) |
C26 | 0.060 (2) | 0.065 (3) | 0.059 (2) | 0.0076 (19) | 0.0245 (19) | −0.001 (2) |
C27 | 0.090 (3) | 0.099 (4) | 0.052 (3) | 0.006 (3) | 0.030 (2) | −0.013 (2) |
C28 | 0.095 (3) | 0.119 (4) | 0.038 (2) | 0.002 (3) | 0.014 (2) | 0.001 (2) |
C29 | 0.067 (2) | 0.093 (3) | 0.046 (2) | 0.012 (2) | 0.0070 (19) | 0.009 (2) |
C30 | 0.051 (2) | 0.059 (2) | 0.0421 (19) | 0.0040 (17) | 0.0103 (16) | 0.0006 (17) |
C31 | 0.045 (2) | 0.044 (2) | 0.048 (2) | 0.0003 (15) | −0.0004 (17) | −0.0001 (16) |
C32 | 0.0358 (17) | 0.051 (2) | 0.047 (2) | 0.0003 (15) | 0.0004 (15) | 0.0033 (17) |
C33 | 0.062 (2) | 0.118 (4) | 0.051 (2) | 0.032 (2) | 0.001 (2) | 0.005 (2) |
C34 | 0.097 (4) | 0.142 (5) | 0.051 (3) | 0.034 (3) | −0.003 (2) | 0.016 (3) |
C35 | 0.068 (3) | 0.098 (4) | 0.085 (4) | 0.016 (3) | −0.021 (3) | 0.024 (3) |
C36 | 0.044 (2) | 0.093 (3) | 0.116 (4) | 0.018 (2) | 0.004 (3) | 0.033 (3) |
C37 | 0.046 (2) | 0.078 (3) | 0.075 (3) | 0.010 (2) | 0.0122 (19) | 0.020 (2) |
B | 0.0384 (19) | 0.048 (3) | 0.035 (2) | 0.0051 (18) | −0.0022 (16) | −0.0023 (18) |
Geometric parameters (Å, º) top
Zn—O1 | 1.920 (2) | C14—C15 | 1.474 (4) |
Zn—N1 | 2.029 (3) | C15—C20 | 1.383 (4) |
Zn—N3 | 2.038 (3) | C15—C16 | 1.396 (4) |
Zn—N5 | 2.081 (2) | C16—C17 | 1.373 (5) |
Zn—C31 | 2.576 (3) | C16—H16 | 0.9300 |
N1—C4 | 1.341 (4) | C17—C18 | 1.368 (5) |
N1—N2 | 1.373 (3) | C17—H17 | 0.9300 |
N2—C2 | 1.352 (4) | C18—C19 | 1.370 (5) |
N2—B | 1.548 (4) | C18—H18 | 0.9300 |
N3—C14 | 1.337 (4) | C19—C20 | 1.383 (5) |
N3—N4 | 1.381 (3) | C19—H19 | 0.9300 |
N4—C12 | 1.354 (4) | C20—H20 | 0.9300 |
N4—B | 1.535 (4) | C21—C22 | 1.491 (4) |
N5—C24 | 1.350 (4) | C21—H21A | 0.9600 |
N5—N6 | 1.372 (3) | C21—H21B | 0.9600 |
N6—C22 | 1.349 (4) | C21—H21C | 0.9600 |
N6—B | 1.552 (4) | C22—C23 | 1.367 (4) |
O1—C31 | 1.288 (4) | C23—C24 | 1.396 (4) |
O2—C31 | 1.226 (4) | C23—H23 | 0.9300 |
C1—C2 | 1.496 (4) | C24—C25 | 1.464 (4) |
C1—H1A | 0.9600 | C25—C30 | 1.380 (4) |
C1—H1B | 0.9600 | C25—C26 | 1.395 (4) |
C1—H1C | 0.9600 | C26—C27 | 1.371 (5) |
C2—C3 | 1.366 (4) | C26—H26 | 0.9300 |
C3—C4 | 1.390 (4) | C27—C28 | 1.367 (6) |
C3—H3 | 0.9300 | C27—H27 | 0.9300 |
C4—C5 | 1.469 (4) | C28—C29 | 1.373 (5) |
C5—C6 | 1.377 (5) | C28—H28 | 0.9300 |
C5—C10 | 1.381 (4) | C29—C30 | 1.383 (4) |
C6—C7 | 1.379 (5) | C29—H29 | 0.9300 |
C6—H6 | 0.9300 | C30—H30 | 0.9300 |
C7—C8 | 1.361 (5) | C31—C32 | 1.496 (4) |
C7—H7 | 0.9300 | C32—C33 | 1.364 (5) |
C8—C9 | 1.362 (5) | C32—C37 | 1.370 (5) |
C8—H8 | 0.9300 | C33—C34 | 1.385 (5) |
C9—C10 | 1.384 (5) | C33—H33 | 0.9300 |
C9—H9 | 0.9300 | C34—C35 | 1.359 (6) |
C10—H10 | 0.9300 | C34—H34 | 0.9300 |
C11—C12 | 1.498 (4) | C35—C36 | 1.340 (6) |
C11—H11A | 0.9600 | C35—H35 | 0.9300 |
C11—H11B | 0.9600 | C36—C37 | 1.377 (5) |
C11—H11C | 0.9600 | C36—H36 | 0.9300 |
C12—C13 | 1.365 (4) | C37—H37 | 0.9300 |
C13—C14 | 1.387 (4) | B—BH | 1.11 (2) |
C13—H13 | 0.9300 | | |
| | | |
O1—Zn—N1 | 128.63 (10) | C20—C15—C16 | 118.9 (3) |
O1—Zn—N3 | 123.21 (10) | C20—C15—C14 | 122.5 (3) |
N1—Zn—N3 | 98.85 (10) | C16—C15—C14 | 118.5 (3) |
O1—Zn—N5 | 113.83 (10) | C17—C16—C15 | 120.2 (4) |
N1—Zn—N5 | 91.52 (10) | C17—C16—H16 | 119.9 |
N3—Zn—N5 | 90.64 (10) | C15—C16—H16 | 119.9 |
O2—Zn—O1 | 56.04 (9) | C18—C17—C16 | 120.5 (4) |
O2—Zn—N3 | 94.53 (9) | C18—C17—H17 | 119.8 |
O2—Zn—N1 | 96.33 (9) | C16—C17—H17 | 119.8 |
O2—Zn—N5 | 169.81 (9) | C17—C18—C19 | 119.8 (4) |
O1—Zn—C31 | 28.86 (10) | C17—C18—H18 | 120.1 |
N1—Zn—C31 | 116.36 (11) | C19—C18—H18 | 120.1 |
N3—Zn—C31 | 108.07 (10) | C18—C19—C20 | 120.7 (4) |
N5—Zn—C31 | 142.37 (10) | C18—C19—H19 | 119.7 |
C4—N1—N2 | 106.6 (2) | C20—C19—H19 | 119.7 |
C4—N1—Zn | 139.8 (2) | C15—C20—C19 | 119.8 (3) |
N2—N1—Zn | 110.70 (19) | C15—C20—H20 | 120.1 |
C2—N2—N1 | 109.6 (3) | C19—C20—H20 | 120.1 |
C2—N2—B | 130.5 (3) | C22—C21—H21A | 109.5 |
N1—N2—B | 120.0 (2) | C22—C21—H21B | 109.5 |
C14—N3—N4 | 107.1 (2) | H21A—C21—H21B | 109.5 |
C14—N3—Zn | 141.0 (2) | C22—C21—H21C | 109.5 |
N4—N3—Zn | 111.58 (18) | H21A—C21—H21C | 109.5 |
C12—N4—N3 | 108.9 (2) | H21B—C21—H21C | 109.5 |
C12—N4—B | 130.8 (3) | N6—C22—C23 | 107.5 (3) |
N3—N4—B | 120.2 (2) | N6—C22—C21 | 123.4 (3) |
C24—N5—N6 | 106.4 (2) | C23—C22—C21 | 129.2 (3) |
C24—N5—Zn | 143.0 (2) | C22—C23—C24 | 106.9 (3) |
N6—N5—Zn | 109.80 (17) | C22—C23—H23 | 126.5 |
C22—N6—N5 | 110.3 (2) | C24—C23—H23 | 126.5 |
C22—N6—B | 128.7 (3) | N5—C24—C23 | 108.9 (3) |
N5—N6—B | 121.0 (2) | N5—C24—C25 | 123.1 (3) |
C31—O1—Zn | 105.1 (2) | C23—C24—C25 | 128.0 (3) |
C2—C1—H1A | 109.5 | C30—C25—C26 | 118.0 (3) |
C2—C1—H1B | 109.5 | C30—C25—C24 | 122.6 (3) |
H1A—C1—H1B | 109.5 | C26—C25—C24 | 119.5 (3) |
C2—C1—H1C | 109.5 | C27—C26—C25 | 120.7 (4) |
H1A—C1—H1C | 109.5 | C27—C26—H26 | 119.7 |
H1B—C1—H1C | 109.5 | C25—C26—H26 | 119.7 |
N2—C2—C3 | 107.8 (3) | C28—C27—C26 | 120.6 (4) |
N2—C2—C1 | 122.4 (3) | C28—C27—H27 | 119.7 |
C3—C2—C1 | 129.8 (3) | C26—C27—H27 | 119.7 |
C2—C3—C4 | 106.6 (3) | C27—C28—C29 | 119.8 (4) |
C2—C3—H3 | 126.7 | C27—C28—H28 | 120.1 |
C4—C3—H3 | 126.7 | C29—C28—H28 | 120.1 |
N1—C4—C3 | 109.4 (3) | C28—C29—C30 | 120.0 (4) |
N1—C4—C5 | 122.5 (3) | C28—C29—H29 | 120.0 |
C3—C4—C5 | 128.1 (3) | C30—C29—H29 | 120.0 |
C6—C5—C10 | 117.1 (3) | C25—C30—C29 | 121.0 (3) |
C6—C5—C4 | 120.9 (3) | C25—C30—H30 | 119.5 |
C10—C5—C4 | 122.0 (3) | C29—C30—H30 | 119.5 |
C5—C6—C7 | 121.4 (4) | O2—C31—O1 | 122.2 (3) |
C5—C6—H6 | 119.3 | O2—C31—C32 | 121.3 (3) |
C7—C6—H6 | 119.3 | O1—C31—C32 | 116.5 (3) |
C8—C7—C6 | 120.4 (4) | O2—C31—Zn | 76.95 (19) |
C8—C7—H7 | 119.8 | O1—C31—Zn | 46.02 (14) |
C6—C7—H7 | 119.8 | C32—C31—Zn | 159.2 (2) |
C7—C8—C9 | 119.7 (4) | C33—C32—C37 | 118.9 (3) |
C7—C8—H8 | 120.2 | C33—C32—C31 | 121.3 (3) |
C9—C8—H8 | 120.2 | C37—C32—C31 | 119.7 (3) |
C8—C9—C10 | 119.9 (4) | C32—C33—C34 | 120.1 (4) |
C8—C9—H9 | 120.0 | C32—C33—H33 | 120.0 |
C10—C9—H9 | 120.0 | C34—C33—H33 | 120.0 |
C5—C10—C9 | 121.5 (3) | C35—C34—C33 | 120.2 (4) |
C5—C10—H10 | 119.3 | C35—C34—H34 | 119.9 |
C9—C10—H10 | 119.3 | C33—C34—H34 | 119.9 |
C12—C11—H11A | 109.5 | C36—C35—C34 | 119.9 (4) |
C12—C11—H11B | 109.5 | C36—C35—H35 | 120.1 |
H11A—C11—H11B | 109.5 | C34—C35—H35 | 120.1 |
C12—C11—H11C | 109.5 | C35—C36—C37 | 120.6 (4) |
H11A—C11—H11C | 109.5 | C35—C36—H36 | 119.7 |
H11B—C11—H11C | 109.5 | C37—C36—H36 | 119.7 |
N4—C12—C13 | 107.8 (3) | C32—C37—C36 | 120.3 (4) |
N4—C12—C11 | 122.7 (3) | C32—C37—H37 | 119.8 |
C13—C12—C11 | 129.5 (3) | C36—C37—H37 | 119.8 |
C12—C13—C14 | 107.0 (3) | N4—B—N2 | 109.4 (2) |
C12—C13—H13 | 126.5 | N4—B—N6 | 109.7 (3) |
C14—C13—H13 | 126.5 | N2—B—N6 | 109.1 (3) |
N3—C14—C13 | 109.1 (3) | N4—B—BH | 110.7 (13) |
N3—C14—C15 | 123.6 (3) | N2—B—BH | 109.2 (13) |
C13—C14—C15 | 127.3 (3) | N6—B—BH | 108.6 (13) |
| | | |
O1—Zn—N1—C4 | −21.7 (4) | N3—C14—C15—C20 | −36.8 (5) |
N3—Zn—N1—C4 | 124.8 (3) | C13—C14—C15—C20 | 140.9 (4) |
N5—Zn—N1—C4 | −144.3 (3) | N3—C14—C15—C16 | 145.6 (3) |
C31—Zn—N1—C4 | 9.5 (4) | C13—C14—C15—C16 | −36.6 (5) |
O1—Zn—N1—N2 | −178.82 (16) | C20—C15—C16—C17 | 0.5 (5) |
N3—Zn—N1—N2 | −32.30 (19) | C14—C15—C16—C17 | 178.2 (3) |
N5—Zn—N1—N2 | 58.59 (19) | C15—C16—C17—C18 | 0.1 (6) |
C31—Zn—N1—N2 | −147.61 (18) | C16—C17—C18—C19 | 0.0 (6) |
C4—N1—N2—C2 | −1.5 (3) | C17—C18—C19—C20 | −0.7 (6) |
Zn—N1—N2—C2 | 163.30 (19) | C16—C15—C20—C19 | −1.2 (5) |
C4—N1—N2—B | 177.7 (3) | C14—C15—C20—C19 | −178.8 (3) |
Zn—N1—N2—B | −17.5 (3) | C18—C19—C20—C15 | 1.3 (6) |
O1—Zn—N3—C14 | 17.1 (4) | N5—N6—C22—C23 | 0.6 (3) |
N1—Zn—N3—C14 | −131.9 (3) | B—N6—C22—C23 | −178.0 (3) |
N5—Zn—N3—C14 | 136.5 (3) | N5—N6—C22—C21 | 179.9 (3) |
C31—Zn—N3—C14 | −10.3 (4) | B—N6—C22—C21 | 1.3 (5) |
O1—Zn—N3—N4 | −169.65 (17) | N6—C22—C23—C24 | −0.2 (4) |
N1—Zn—N3—N4 | 41.4 (2) | C21—C22—C23—C24 | −179.4 (3) |
N5—Zn—N3—N4 | −50.29 (19) | N6—N5—C24—C23 | 0.6 (3) |
C31—Zn—N3—N4 | 162.91 (18) | Zn—N5—C24—C23 | −167.1 (3) |
C14—N3—N4—C12 | 0.1 (3) | N6—N5—C24—C25 | −179.8 (3) |
Zn—N3—N4—C12 | −175.4 (2) | Zn—N5—C24—C25 | 12.5 (5) |
C14—N3—N4—B | 176.2 (3) | C22—C23—C24—N5 | −0.3 (4) |
Zn—N3—N4—B | 0.6 (3) | C22—C23—C24—C25 | −179.8 (3) |
O1—Zn—N5—C24 | −10.4 (4) | N5—C24—C25—C30 | 25.3 (5) |
N1—Zn—N5—C24 | 123.6 (3) | C23—C24—C25—C30 | −155.2 (3) |
N3—Zn—N5—C24 | −137.6 (3) | N5—C24—C25—C26 | −155.9 (3) |
C31—Zn—N5—C24 | −16.1 (4) | C23—C24—C25—C26 | 23.6 (5) |
O1—Zn—N5—N6 | −177.86 (17) | C30—C25—C26—C27 | −1.9 (5) |
N1—Zn—N5—N6 | −43.88 (18) | C24—C25—C26—C27 | 179.2 (3) |
N3—Zn—N5—N6 | 55.00 (19) | C25—C26—C27—C28 | 0.5 (6) |
C31—Zn—N5—N6 | 176.50 (17) | C26—C27—C28—C29 | 0.9 (7) |
C24—N5—N6—C22 | −0.8 (3) | C27—C28—C29—C30 | −1.0 (7) |
Zn—N5—N6—C22 | 171.39 (19) | C26—C25—C30—C29 | 1.9 (5) |
C24—N5—N6—B | 177.9 (3) | C24—C25—C30—C29 | −179.2 (3) |
Zn—N5—N6—B | −9.9 (3) | C28—C29—C30—C25 | −0.5 (6) |
N1—Zn—O1—C31 | 74.2 (2) | Zn—O1—C31—O2 | −12.0 (4) |
N3—Zn—O1—C31 | −65.2 (2) | Zn—O1—C31—C32 | 166.1 (2) |
N5—Zn—O1—C31 | −172.9 (2) | O1—Zn—C31—O2 | 169.6 (3) |
N1—N2—C2—C3 | 1.3 (3) | N1—Zn—C31—O2 | 46.6 (2) |
B—N2—C2—C3 | −177.7 (3) | N3—Zn—C31—O2 | −63.4 (2) |
N1—N2—C2—C1 | −176.8 (3) | N5—Zn—C31—O2 | −179.68 (17) |
B—N2—C2—C1 | 4.1 (5) | N1—Zn—C31—O1 | −123.0 (2) |
N2—C2—C3—C4 | −0.6 (4) | N3—Zn—C31—O1 | 127.0 (2) |
C1—C2—C3—C4 | 177.3 (3) | N5—Zn—C31—O1 | 10.7 (3) |
N2—N1—C4—C3 | 1.1 (3) | O1—Zn—C31—C32 | −37.4 (6) |
Zn—N1—C4—C3 | −156.6 (2) | N1—Zn—C31—C32 | −160.4 (6) |
N2—N1—C4—C5 | −177.9 (3) | N3—Zn—C31—C32 | 89.6 (7) |
Zn—N1—C4—C5 | 24.4 (5) | N5—Zn—C31—C32 | −26.7 (7) |
C2—C3—C4—N1 | −0.3 (4) | O2—C31—C32—C33 | −177.1 (4) |
C2—C3—C4—C5 | 178.6 (3) | O1—C31—C32—C33 | 4.8 (5) |
N1—C4—C5—C6 | −160.4 (3) | Zn—C31—C32—C33 | 34.1 (9) |
C3—C4—C5—C6 | 20.8 (5) | O2—C31—C32—C37 | 5.7 (5) |
N1—C4—C5—C10 | 20.9 (5) | O1—C31—C32—C37 | −172.4 (3) |
C3—C4—C5—C10 | −157.8 (3) | Zn—C31—C32—C37 | −143.1 (6) |
C10—C5—C6—C7 | −1.2 (6) | C37—C32—C33—C34 | −0.4 (6) |
C4—C5—C6—C7 | −179.9 (3) | C31—C32—C33—C34 | −177.6 (4) |
C5—C6—C7—C8 | 0.4 (6) | C32—C33—C34—C35 | 0.3 (8) |
C6—C7—C8—C9 | 0.9 (7) | C33—C34—C35—C36 | 0.0 (8) |
C7—C8—C9—C10 | −1.4 (7) | C34—C35—C36—C37 | −0.2 (8) |
C6—C5—C10—C9 | 0.6 (5) | C33—C32—C37—C36 | 0.2 (6) |
C4—C5—C10—C9 | 179.4 (3) | C31—C32—C37—C36 | 177.5 (4) |
C8—C9—C10—C5 | 0.6 (6) | C35—C36—C37—C32 | 0.1 (7) |
N3—N4—C12—C13 | −0.2 (4) | C12—N4—B—N2 | 115.4 (3) |
B—N4—C12—C13 | −175.7 (3) | N3—N4—B—N2 | −59.7 (3) |
N3—N4—C12—C11 | −179.5 (3) | C12—N4—B—N6 | −124.9 (3) |
B—N4—C12—C11 | 5.1 (5) | N3—N4—B—N6 | 60.0 (3) |
N4—C12—C13—C14 | 0.2 (4) | C2—N2—B—N4 | −109.2 (3) |
C11—C12—C13—C14 | 179.4 (3) | N1—N2—B—N4 | 71.9 (3) |
N4—N3—C14—C13 | 0.0 (3) | C2—N2—B—N6 | 130.7 (3) |
Zn—N3—C14—C13 | 173.4 (3) | N1—N2—B—N6 | −48.2 (3) |
N4—N3—C14—C15 | 178.1 (3) | C22—N6—B—N4 | 124.9 (3) |
Zn—N3—C14—C15 | −8.5 (5) | N5—N6—B—N4 | −53.5 (3) |
C12—C13—C14—N3 | −0.1 (4) | C22—N6—B—N2 | −115.2 (3) |
C12—C13—C14—C15 | −178.1 (3) | N5—N6—B—N2 | 66.4 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C30—H30···O1 | 0.93 | 2.47 | 3.111 (4) | 126 |
C16—H16···O2i | 0.93 | 2.55 | 3.438 (5) | 160 |
Symmetry code: (i) −x, −y+1, −z+1. |