In the title compound, [Zn(C
12H
7O
4)(C
19H
12N
4O)
2](C
12H
7O
4)·2H
2O or [Zn(
L)
2(HNDC)](HNDC)·2H
2O, where HNDC is the naphthalene-1,4-dicarboxylate monoanion and
L is 4-(1
H-1,3,7,8-tetraazacyclopenta[
l]phenanthren-2-yl)phenol, the Zn
II atom is five-coordinated by four N atoms from two
L ligands, and one O atom from the HNDC monoanion in an approximate trigonal–bipyramidal geometry. Aromatic π–π stacking interactions between
L ligands, and N—H
O, O—H
O and N—H
O hydrogen bonds, stabilize the crystal structure.
Supporting information
CCDC reference: 627460
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.005 Å
- R factor = 0.062
- wR factor = 0.163
- Data-to-parameter ratio = 15.1
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT094_ALERT_2_B Ratio of Maximum / Minimum Residual Density .... 4.36
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C44
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.71 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C56
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
4 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
3 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
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.
(Naphthalene-1,4-dicarboxylato)bis[4-(1
H-1,3,7,8-
tetraazacyclopenta[
l]phenanthren-2-yl)phenol]zinc(II)
naphthalene-1,4-dicarboxylate dihydrate
top
Crystal data top
[Zn(C12H7O4)(C19H12N4O)2](C12H7O4)·2H2O | F(000) = 2384 |
Mr = 1156.41 | Dx = 1.516 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 30831 reflections |
a = 17.141 (3) Å | θ = 3.0–27.5° |
b = 16.729 (3) Å | µ = 0.56 mm−1 |
c = 19.595 (4) Å | T = 292 K |
β = 115.60 (3)° | Block, yellow |
V = 5067 (2) Å3 | 0.30 × 0.27 × 0.24 mm |
Z = 4 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 11528 independent reflections |
Radiation source: rotorating anode | 7908 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.070 |
Detector resolution: 10.0 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ω scans | h = −22→22 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −21→21 |
Tmin = 0.840, Tmax = 0.881 | l = −25→25 |
48539 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)] = 0.062 | Hydrogen site location: constr |
wR(F2) = 0.163 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0732P)2 + 4.9842P] where P = (Fo2 + 2Fc2)/3 |
11528 reflections | (Δ/σ)max = 0.001 |
764 parameters | Δρmax = 2.10 e Å−3 |
4 restraints | 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 | |
C1 | 0.7137 (2) | 0.1373 (2) | 0.01021 (19) | 0.0408 (8) | |
H1 | 0.6946 | 0.0921 | 0.0262 | 0.049* | |
C2 | 0.7123 (3) | 0.1367 (2) | −0.0611 (2) | 0.0464 (9) | |
H2 | 0.6937 | 0.0916 | −0.0916 | 0.056* | |
C3 | 0.7383 (2) | 0.2031 (2) | −0.08582 (19) | 0.0402 (8) | |
H3A | 0.7368 | 0.2040 | −0.1338 | 0.048* | |
C4 | 0.7671 (2) | 0.26969 (19) | −0.03858 (17) | 0.0330 (7) | |
C5 | 0.7681 (2) | 0.26520 (18) | 0.03321 (17) | 0.0310 (6) | |
C6 | 0.79748 (19) | 0.33113 (19) | 0.08639 (16) | 0.0308 (6) | |
C7 | 0.8265 (2) | 0.40297 (19) | 0.06760 (18) | 0.0359 (7) | |
C8 | 0.8520 (2) | 0.4646 (2) | 0.1204 (2) | 0.0430 (8) | |
H8A | 0.8707 | 0.5131 | 0.1094 | 0.052* | |
C9 | 0.8494 (2) | 0.4534 (2) | 0.1887 (2) | 0.0457 (8) | |
H9A | 0.8662 | 0.4941 | 0.2245 | 0.055* | |
C10 | 0.8215 (2) | 0.3806 (2) | 0.20377 (19) | 0.0402 (8) | |
H10A | 0.8210 | 0.3732 | 0.2506 | 0.048* | |
C11 | 0.8270 (2) | 0.40587 (19) | −0.00556 (18) | 0.0355 (7) | |
C12 | 0.7986 (2) | 0.34231 (19) | −0.05466 (18) | 0.0349 (7) | |
C13 | 0.8424 (2) | 0.4406 (2) | −0.10367 (19) | 0.0418 (8) | |
C14 | 0.8672 (2) | 0.4842 (2) | −0.1557 (2) | 0.0426 (8) | |
C15 | 0.9119 (3) | 0.5550 (2) | −0.1318 (2) | 0.0516 (10) | |
H15 | 0.9227 | 0.5750 | −0.0842 | 0.062* | |
C16 | 0.9408 (3) | 0.5967 (2) | −0.1771 (2) | 0.0523 (10) | |
H16 | 0.9698 | 0.6450 | −0.1605 | 0.063* | |
C17 | 0.9267 (2) | 0.5668 (2) | −0.24702 (19) | 0.0434 (8) | |
C18 | 0.8815 (3) | 0.4966 (2) | −0.2717 (2) | 0.0548 (10) | |
H18 | 0.8712 | 0.4764 | −0.3190 | 0.066* | |
C19 | 0.8513 (3) | 0.4558 (2) | −0.2268 (2) | 0.0551 (10) | |
H19 | 0.8201 | 0.4087 | −0.2445 | 0.066* | |
C20 | 0.8612 (2) | 0.0587 (2) | 0.18020 (17) | 0.0353 (7) | |
H20 | 0.8585 | 0.0731 | 0.1334 | 0.042* | |
C21 | 0.9000 (2) | −0.0143 (2) | 0.21184 (18) | 0.0391 (7) | |
H21 | 0.9216 | −0.0478 | 0.1862 | 0.047* | |
C22 | 0.9053 (2) | −0.0354 (2) | 0.28104 (18) | 0.0365 (7) | |
H22 | 0.9303 | −0.0838 | 0.3030 | 0.044* | |
C23 | 0.8729 (2) | 0.01632 (18) | 0.31873 (16) | 0.0304 (6) | |
C24 | 0.83434 (19) | 0.08871 (18) | 0.28267 (15) | 0.0292 (6) | |
C25 | 0.7995 (2) | 0.14502 (18) | 0.31853 (16) | 0.0298 (6) | |
C26 | 0.7237 (2) | 0.2617 (2) | 0.30748 (19) | 0.0420 (8) | |
H26 | 0.6966 | 0.3068 | 0.2795 | 0.050* | |
C27 | 0.7232 (3) | 0.2510 (2) | 0.3772 (2) | 0.0451 (8) | |
H27 | 0.6956 | 0.2876 | 0.3951 | 0.054* | |
C28 | 0.7642 (2) | 0.1852 (2) | 0.41958 (19) | 0.0414 (8) | |
H28 | 0.7657 | 0.1773 | 0.4671 | 0.050* | |
C29 | 0.8036 (2) | 0.13036 (18) | 0.39085 (17) | 0.0322 (7) | |
C30 | 0.8453 (2) | 0.05765 (19) | 0.42772 (16) | 0.0318 (7) | |
C31 | 0.8753 (2) | 0.00364 (18) | 0.39148 (16) | 0.0315 (6) | |
C32 | 0.9205 (2) | −0.09796 (18) | 0.56673 (16) | 0.0318 (6) | |
C33 | 0.9627 (2) | −0.1687 (2) | 0.56822 (18) | 0.0384 (7) | |
H33 | 0.9717 | −0.1833 | 0.5264 | 0.046* | |
C34 | 0.9919 (2) | −0.2181 (2) | 0.63088 (18) | 0.0398 (8) | |
H34 | 1.0199 | −0.2657 | 0.6309 | 0.048* | |
C35 | 0.9792 (2) | −0.19646 (19) | 0.69365 (17) | 0.0345 (7) | |
C36 | 0.9354 (2) | −0.1267 (2) | 0.69280 (17) | 0.0367 (7) | |
H36 | 0.9253 | −0.1129 | 0.7342 | 0.044* | |
C37 | 0.9070 (2) | −0.0778 (2) | 0.62981 (17) | 0.0368 (7) | |
H37 | 0.8783 | −0.0305 | 0.6295 | 0.044* | |
C38 | 0.8938 (2) | −0.04264 (19) | 0.50257 (16) | 0.0316 (6) | |
C39 | 0.5774 (2) | 0.2170 (2) | 0.11505 (17) | 0.0391 (8) | |
C40 | 0.4832 (2) | 0.1959 (2) | 0.08709 (19) | 0.0382 (7) | |
C41 | 0.4406 (3) | 0.2260 (2) | 0.1260 (2) | 0.0531 (10) | |
H41 | 0.4679 | 0.2636 | 0.1640 | 0.064* | |
C42 | 0.3568 (3) | 0.2016 (2) | 0.1101 (2) | 0.0504 (9) | |
H42 | 0.3301 | 0.2217 | 0.1389 | 0.060* | |
C43 | 0.3129 (2) | 0.1486 (2) | 0.05287 (19) | 0.0387 (7) | |
C44 | 0.2235 (2) | 0.1263 (2) | 0.0403 (2) | 0.0459 (8) | |
C45 | 0.3535 (2) | 0.11956 (19) | 0.00755 (17) | 0.0341 (7) | |
C46 | 0.3114 (2) | 0.0682 (2) | −0.05575 (19) | 0.0416 (8) | |
H46 | 0.2551 | 0.0513 | −0.0681 | 0.050* | |
C47 | 0.3518 (3) | 0.0430 (2) | −0.0989 (2) | 0.0461 (9) | |
H47 | 0.3228 | 0.0097 | −0.1402 | 0.055* | |
C48 | 0.4359 (3) | 0.0668 (2) | −0.0810 (2) | 0.0462 (9) | |
H48 | 0.4629 | 0.0494 | −0.1105 | 0.055* | |
C49 | 0.4794 (2) | 0.1156 (2) | −0.02063 (18) | 0.0403 (8) | |
H49 | 0.5357 | 0.1313 | −0.0096 | 0.048* | |
C50 | 0.4399 (2) | 0.14277 (19) | 0.02540 (17) | 0.0336 (7) | |
C51 | 1.0030 (2) | 0.1676 (2) | 0.08843 (18) | 0.0372 (7) | |
C52 | 0.9672 (2) | 0.1505 (2) | 0.00451 (18) | 0.0374 (7) | |
C53 | 0.9249 (3) | 0.0801 (2) | −0.0238 (2) | 0.0486 (9) | |
H53 | 0.9170 | 0.0436 | 0.0084 | 0.058* | |
C54 | 0.8933 (3) | 0.0625 (2) | −0.1017 (2) | 0.0532 (10) | |
H54 | 0.8659 | 0.0139 | −0.1200 | 0.064* | |
C55 | 0.9025 (2) | 0.1156 (2) | −0.15019 (19) | 0.0471 (9) | |
C56 | 0.8649 (3) | 0.0891 (3) | −0.2312 (2) | 0.0630 (12) | |
C57 | 0.9469 (2) | 0.1892 (2) | −0.12275 (19) | 0.0452 (8) | |
C58 | 0.9635 (3) | 0.2460 (3) | −0.1688 (2) | 0.0585 (11) | |
H58 | 0.9435 | 0.2359 | −0.2203 | 0.070* | |
C59 | 1.0073 (3) | 0.3139 (3) | −0.1402 (3) | 0.0710 (13) | |
H59 | 1.0175 | 0.3495 | −0.1719 | 0.085* | |
C60 | 1.0380 (3) | 0.3319 (3) | −0.0628 (2) | 0.0677 (12) | |
H60 | 1.0674 | 0.3794 | −0.0435 | 0.081* | |
C61 | 1.0243 (3) | 0.2792 (2) | −0.0167 (2) | 0.0534 (10) | |
H61 | 1.0445 | 0.2914 | 0.0344 | 0.064* | |
C62 | 0.9802 (2) | 0.2063 (2) | −0.04393 (18) | 0.0405 (8) | |
N1 | 0.74122 (17) | 0.19933 (16) | 0.05644 (15) | 0.0347 (6) | |
N2 | 0.79574 (17) | 0.32137 (16) | 0.15451 (14) | 0.0339 (6) | |
N3 | 0.80802 (19) | 0.36529 (16) | −0.11782 (15) | 0.0384 (6) | |
H3 | 0.7949 | 0.3378 | −0.1584 | 0.046* | |
N4 | 0.8541 (2) | 0.46778 (17) | −0.03590 (16) | 0.0410 (7) | |
N5 | 0.82815 (17) | 0.10803 (15) | 0.21339 (13) | 0.0316 (6) | |
N6 | 0.76086 (18) | 0.21123 (15) | 0.27834 (14) | 0.0347 (6) | |
N7 | 0.85796 (17) | 0.02881 (16) | 0.49755 (14) | 0.0334 (6) | |
N8 | 0.90563 (17) | −0.06056 (16) | 0.43926 (14) | 0.0342 (6) | |
H8B | 0.9277 | −0.1036 | 0.4312 | 0.041* | |
O1 | 0.62927 (16) | 0.15975 (17) | 0.12892 (14) | 0.0483 (6) | |
O2 | 0.59966 (18) | 0.28844 (16) | 0.12537 (14) | 0.0521 (7) | |
O3 | 0.1677 (2) | 0.1013 (3) | −0.0181 (2) | 0.0956 (13) | |
O4 | 0.2103 (2) | 0.1395 (3) | 0.09875 (18) | 0.1012 (15) | |
H4 | 0.1607 | 0.1266 | 0.0898 | 0.152* | |
O5 | 0.95177 (17) | 0.18772 (18) | 0.11392 (14) | 0.0552 (7) | |
O6 | 1.08248 (17) | 0.1607 (2) | 0.12627 (14) | 0.0644 (8) | |
O7 | 0.8632 (3) | 0.0188 (2) | −0.2489 (2) | 0.1145 (16) | |
O8 | 0.8252 (2) | 0.1422 (2) | −0.28120 (16) | 0.0798 (10) | |
H8 | 0.8070 | 0.1222 | −0.3235 | 0.120* | |
O9 | 1.01236 (17) | −0.24543 (15) | 0.75489 (13) | 0.0453 (6) | |
H9 | 1.0021 | −0.2268 | 0.7889 | 0.068* | |
O10 | 0.95701 (18) | 0.60334 (17) | −0.29258 (14) | 0.0545 (7) | |
H10 | 0.9834 | 0.6439 | −0.2718 | 0.082* | |
Zn1 | 0.74898 (2) | 0.20909 (2) | 0.16604 (2) | 0.03441 (12) | |
O1W | 0.7679 (2) | 0.09929 (17) | 0.57649 (15) | 0.0526 (7) | |
O2W | 0.2255 (2) | 0.2271 (2) | 0.25048 (16) | 0.0633 (8) | |
HW11 | 0.812 (3) | 0.082 (4) | 0.566 (4) | 0.14 (3)* | |
HW12 | 0.725 (3) | 0.062 (3) | 0.566 (3) | 0.11 (2)* | |
HW21 | 0.260 (3) | 0.260 (3) | 0.240 (3) | 0.10 (2)* | |
HW22 | 0.175 (2) | 0.210 (3) | 0.214 (3) | 0.11 (2)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.046 (2) | 0.0369 (18) | 0.0380 (17) | −0.0055 (15) | 0.0163 (15) | 0.0062 (15) |
C2 | 0.058 (2) | 0.0371 (19) | 0.0379 (18) | −0.0077 (16) | 0.0150 (17) | −0.0033 (15) |
C3 | 0.048 (2) | 0.0405 (18) | 0.0319 (16) | −0.0048 (16) | 0.0173 (15) | 0.0007 (14) |
C4 | 0.0309 (16) | 0.0350 (16) | 0.0311 (15) | 0.0033 (13) | 0.0116 (13) | 0.0073 (13) |
C5 | 0.0292 (15) | 0.0326 (16) | 0.0285 (14) | 0.0023 (12) | 0.0100 (12) | 0.0076 (13) |
C6 | 0.0303 (15) | 0.0340 (16) | 0.0270 (14) | 0.0037 (13) | 0.0113 (12) | 0.0076 (13) |
C7 | 0.0387 (18) | 0.0350 (17) | 0.0331 (16) | 0.0016 (14) | 0.0147 (14) | 0.0065 (14) |
C8 | 0.053 (2) | 0.0333 (17) | 0.0442 (19) | −0.0062 (15) | 0.0228 (17) | −0.0007 (15) |
C9 | 0.054 (2) | 0.044 (2) | 0.0416 (19) | −0.0056 (17) | 0.0222 (17) | −0.0057 (16) |
C10 | 0.0438 (19) | 0.0438 (19) | 0.0339 (16) | −0.0010 (15) | 0.0176 (15) | −0.0004 (15) |
C11 | 0.0400 (18) | 0.0343 (16) | 0.0347 (16) | −0.0005 (14) | 0.0184 (14) | 0.0046 (14) |
C12 | 0.0364 (17) | 0.0363 (17) | 0.0332 (16) | 0.0005 (14) | 0.0161 (14) | 0.0066 (14) |
C13 | 0.050 (2) | 0.0381 (18) | 0.0404 (18) | −0.0030 (15) | 0.0228 (16) | 0.0062 (15) |
C14 | 0.050 (2) | 0.0410 (19) | 0.0406 (18) | −0.0036 (16) | 0.0228 (16) | 0.0075 (15) |
C15 | 0.070 (3) | 0.050 (2) | 0.043 (2) | −0.0140 (19) | 0.0336 (19) | −0.0034 (17) |
C16 | 0.068 (3) | 0.049 (2) | 0.047 (2) | −0.0156 (19) | 0.032 (2) | −0.0019 (18) |
C17 | 0.051 (2) | 0.046 (2) | 0.0360 (17) | −0.0022 (16) | 0.0208 (16) | 0.0100 (15) |
C18 | 0.078 (3) | 0.050 (2) | 0.0384 (19) | −0.011 (2) | 0.0270 (19) | 0.0037 (17) |
C19 | 0.078 (3) | 0.048 (2) | 0.0385 (19) | −0.018 (2) | 0.0243 (19) | −0.0001 (17) |
C20 | 0.0360 (17) | 0.0459 (19) | 0.0235 (14) | −0.0042 (14) | 0.0123 (13) | 0.0040 (13) |
C21 | 0.0427 (19) | 0.0457 (19) | 0.0319 (16) | 0.0059 (15) | 0.0189 (15) | 0.0008 (15) |
C22 | 0.0388 (18) | 0.0360 (17) | 0.0340 (16) | 0.0032 (14) | 0.0150 (14) | 0.0018 (14) |
C23 | 0.0317 (16) | 0.0326 (16) | 0.0240 (14) | −0.0020 (12) | 0.0092 (12) | −0.0006 (12) |
C24 | 0.0315 (15) | 0.0303 (15) | 0.0232 (13) | −0.0053 (12) | 0.0094 (12) | 0.0020 (12) |
C25 | 0.0324 (16) | 0.0289 (15) | 0.0245 (14) | −0.0037 (12) | 0.0091 (12) | 0.0012 (12) |
C26 | 0.056 (2) | 0.0314 (17) | 0.0366 (17) | 0.0063 (15) | 0.0186 (16) | 0.0045 (14) |
C27 | 0.061 (2) | 0.0393 (18) | 0.0397 (18) | 0.0080 (17) | 0.0256 (18) | −0.0021 (16) |
C28 | 0.059 (2) | 0.0373 (18) | 0.0307 (16) | 0.0022 (16) | 0.0216 (16) | 0.0014 (14) |
C29 | 0.0404 (17) | 0.0284 (15) | 0.0268 (14) | −0.0018 (13) | 0.0136 (13) | 0.0001 (12) |
C30 | 0.0358 (17) | 0.0346 (16) | 0.0239 (14) | −0.0016 (13) | 0.0119 (13) | 0.0022 (12) |
C31 | 0.0391 (17) | 0.0290 (15) | 0.0249 (14) | 0.0005 (13) | 0.0126 (13) | 0.0048 (12) |
C32 | 0.0362 (16) | 0.0343 (16) | 0.0227 (13) | −0.0046 (13) | 0.0107 (12) | 0.0022 (12) |
C33 | 0.051 (2) | 0.0378 (18) | 0.0283 (15) | −0.0005 (15) | 0.0188 (15) | −0.0002 (14) |
C34 | 0.051 (2) | 0.0353 (17) | 0.0311 (16) | 0.0046 (15) | 0.0158 (15) | 0.0039 (14) |
C35 | 0.0379 (17) | 0.0352 (17) | 0.0265 (14) | −0.0055 (13) | 0.0103 (13) | 0.0038 (13) |
C36 | 0.0414 (18) | 0.0443 (19) | 0.0266 (15) | −0.0011 (15) | 0.0168 (14) | 0.0018 (14) |
C37 | 0.0421 (18) | 0.0383 (17) | 0.0308 (15) | 0.0027 (14) | 0.0165 (14) | 0.0040 (14) |
C38 | 0.0355 (16) | 0.0334 (16) | 0.0237 (14) | −0.0053 (13) | 0.0107 (12) | 0.0017 (12) |
C39 | 0.0408 (18) | 0.051 (2) | 0.0253 (15) | −0.0116 (17) | 0.0145 (14) | −0.0055 (15) |
C40 | 0.0374 (18) | 0.0425 (19) | 0.0351 (16) | −0.0060 (14) | 0.0162 (14) | −0.0055 (14) |
C41 | 0.051 (2) | 0.062 (2) | 0.051 (2) | −0.0183 (19) | 0.0263 (18) | −0.0272 (19) |
C42 | 0.051 (2) | 0.062 (2) | 0.049 (2) | −0.0042 (18) | 0.0309 (18) | −0.0132 (19) |
C43 | 0.0341 (17) | 0.0459 (19) | 0.0374 (17) | −0.0015 (14) | 0.0166 (14) | 0.0019 (15) |
C44 | 0.0384 (19) | 0.059 (2) | 0.0434 (19) | 0.0000 (17) | 0.0206 (17) | 0.0059 (18) |
C45 | 0.0363 (17) | 0.0322 (16) | 0.0324 (15) | 0.0018 (13) | 0.0137 (13) | 0.0050 (13) |
C46 | 0.0410 (19) | 0.0378 (18) | 0.0418 (18) | −0.0093 (15) | 0.0140 (15) | −0.0038 (15) |
C47 | 0.056 (2) | 0.0374 (18) | 0.0431 (19) | −0.0085 (16) | 0.0200 (17) | −0.0101 (16) |
C48 | 0.060 (2) | 0.048 (2) | 0.0380 (18) | 0.0016 (18) | 0.0281 (17) | −0.0059 (16) |
C49 | 0.0425 (19) | 0.0459 (19) | 0.0362 (17) | −0.0031 (15) | 0.0204 (15) | −0.0012 (15) |
C50 | 0.0371 (17) | 0.0318 (16) | 0.0325 (15) | 0.0018 (13) | 0.0155 (14) | 0.0025 (13) |
C51 | 0.0357 (18) | 0.0468 (19) | 0.0319 (16) | −0.0008 (15) | 0.0173 (14) | 0.0057 (15) |
C52 | 0.0328 (17) | 0.0480 (19) | 0.0310 (16) | 0.0003 (14) | 0.0134 (14) | 0.0006 (15) |
C53 | 0.054 (2) | 0.052 (2) | 0.0428 (19) | −0.0058 (18) | 0.0230 (17) | 0.0010 (17) |
C54 | 0.057 (2) | 0.050 (2) | 0.048 (2) | −0.0032 (18) | 0.0178 (19) | −0.0081 (18) |
C55 | 0.048 (2) | 0.056 (2) | 0.0340 (17) | 0.0084 (18) | 0.0145 (16) | −0.0069 (17) |
C56 | 0.077 (3) | 0.066 (3) | 0.042 (2) | 0.022 (2) | 0.022 (2) | −0.008 (2) |
C57 | 0.047 (2) | 0.058 (2) | 0.0324 (17) | 0.0091 (17) | 0.0191 (16) | 0.0062 (16) |
C58 | 0.068 (3) | 0.076 (3) | 0.0357 (19) | −0.003 (2) | 0.0261 (19) | 0.009 (2) |
C59 | 0.079 (3) | 0.086 (3) | 0.054 (2) | −0.011 (3) | 0.034 (2) | 0.025 (2) |
C60 | 0.076 (3) | 0.069 (3) | 0.054 (2) | −0.020 (2) | 0.025 (2) | 0.006 (2) |
C61 | 0.060 (2) | 0.062 (3) | 0.0347 (18) | −0.014 (2) | 0.0171 (18) | −0.0013 (17) |
C62 | 0.0400 (18) | 0.053 (2) | 0.0286 (15) | 0.0016 (16) | 0.0146 (14) | 0.0030 (15) |
N1 | 0.0353 (14) | 0.0350 (14) | 0.0315 (13) | −0.0029 (11) | 0.0123 (11) | 0.0064 (12) |
N2 | 0.0332 (14) | 0.0368 (14) | 0.0282 (13) | 0.0001 (11) | 0.0099 (11) | 0.0053 (11) |
N3 | 0.0477 (17) | 0.0382 (15) | 0.0339 (14) | −0.0023 (13) | 0.0219 (13) | 0.0053 (12) |
N4 | 0.0540 (18) | 0.0373 (15) | 0.0384 (15) | −0.0058 (13) | 0.0262 (14) | 0.0036 (12) |
N5 | 0.0342 (14) | 0.0350 (14) | 0.0245 (12) | −0.0042 (11) | 0.0118 (11) | 0.0041 (11) |
N6 | 0.0415 (15) | 0.0325 (14) | 0.0271 (12) | −0.0003 (12) | 0.0120 (11) | 0.0027 (11) |
N7 | 0.0422 (15) | 0.0351 (14) | 0.0239 (12) | −0.0005 (12) | 0.0153 (11) | 0.0019 (11) |
N8 | 0.0429 (15) | 0.0327 (14) | 0.0271 (12) | 0.0034 (12) | 0.0151 (12) | 0.0054 (11) |
O1 | 0.0387 (14) | 0.0594 (16) | 0.0454 (14) | −0.0042 (12) | 0.0168 (11) | −0.0071 (12) |
O2 | 0.0542 (16) | 0.0525 (16) | 0.0431 (14) | −0.0184 (13) | 0.0150 (12) | −0.0015 (12) |
O3 | 0.061 (2) | 0.152 (4) | 0.088 (3) | −0.042 (2) | 0.046 (2) | −0.048 (3) |
O4 | 0.0425 (18) | 0.209 (5) | 0.0606 (19) | −0.021 (2) | 0.0305 (16) | −0.028 (2) |
O5 | 0.0448 (15) | 0.089 (2) | 0.0346 (13) | 0.0104 (14) | 0.0197 (12) | 0.0050 (13) |
O6 | 0.0353 (14) | 0.122 (3) | 0.0340 (13) | 0.0005 (15) | 0.0127 (11) | −0.0053 (15) |
O7 | 0.180 (5) | 0.081 (3) | 0.065 (2) | 0.033 (3) | 0.036 (3) | −0.017 (2) |
O8 | 0.110 (3) | 0.076 (2) | 0.0348 (14) | 0.019 (2) | 0.0144 (16) | −0.0083 (15) |
O9 | 0.0653 (17) | 0.0428 (13) | 0.0297 (11) | 0.0096 (12) | 0.0224 (12) | 0.0113 (10) |
O10 | 0.0671 (18) | 0.0601 (17) | 0.0417 (14) | −0.0127 (14) | 0.0286 (13) | 0.0085 (12) |
Zn1 | 0.0381 (2) | 0.0357 (2) | 0.02697 (19) | −0.00311 (16) | 0.01175 (15) | 0.00712 (15) |
O1W | 0.069 (2) | 0.0536 (16) | 0.0360 (13) | 0.0001 (15) | 0.0234 (14) | −0.0022 (12) |
O2W | 0.073 (2) | 0.066 (2) | 0.0404 (15) | −0.0039 (17) | 0.0153 (15) | 0.0024 (14) |
Geometric parameters (Å, º) top
C1—N1 | 1.323 (4) | C35—O9 | 1.358 (4) |
C1—C2 | 1.386 (5) | C35—C36 | 1.383 (5) |
C1—H1 | 0.93 | C36—C37 | 1.383 (4) |
C2—C3 | 1.361 (5) | C36—H36 | 0.93 |
C2—H2 | 0.93 | C37—H37 | 0.93 |
C3—C4 | 1.396 (5) | C38—N7 | 1.328 (4) |
C3—H3A | 0.93 | C38—N8 | 1.374 (4) |
C4—C5 | 1.402 (4) | C39—O2 | 1.244 (4) |
C4—C12 | 1.419 (4) | C39—O1 | 1.254 (4) |
C5—N1 | 1.347 (4) | C39—C40 | 1.506 (5) |
C5—C6 | 1.450 (4) | C40—C41 | 1.361 (5) |
C6—N2 | 1.358 (4) | C40—C50 | 1.424 (4) |
C6—C7 | 1.409 (4) | C41—C42 | 1.392 (5) |
C7—C8 | 1.390 (5) | C41—H41 | 0.93 |
C7—C11 | 1.438 (4) | C42—C43 | 1.372 (5) |
C8—C9 | 1.372 (5) | C42—H42 | 0.93 |
C8—H8A | 0.93 | C43—C45 | 1.430 (4) |
C9—C10 | 1.385 (5) | C43—C44 | 1.490 (5) |
C9—H9A | 0.93 | C44—O3 | 1.205 (5) |
C10—N2 | 1.319 (4) | C44—O4 | 1.280 (5) |
C10—H10A | 0.93 | C45—C50 | 1.421 (4) |
C11—N4 | 1.371 (4) | C45—C46 | 1.423 (5) |
C11—C12 | 1.374 (5) | C46—C47 | 1.371 (5) |
C12—N3 | 1.370 (4) | C46—H46 | 0.93 |
C13—N4 | 1.334 (4) | C47—C48 | 1.387 (5) |
C13—N3 | 1.368 (4) | C47—H47 | 0.93 |
C13—C14 | 1.458 (4) | C48—C49 | 1.364 (5) |
C14—C15 | 1.378 (5) | C48—H48 | 0.9300 |
C14—C19 | 1.384 (5) | C49—C50 | 1.416 (4) |
C15—C16 | 1.380 (5) | C49—H49 | 0.93 |
C15—H15 | 0.93 | C51—O5 | 1.230 (4) |
C16—C17 | 1.378 (5) | C51—O6 | 1.244 (4) |
C16—H16 | 0.93 | C51—C52 | 1.514 (4) |
C17—O10 | 1.357 (4) | C52—C53 | 1.367 (5) |
C17—C18 | 1.375 (5) | C52—C62 | 1.416 (5) |
C18—C19 | 1.377 (5) | C53—C54 | 1.412 (5) |
C18—H18 | 0.93 | C53—H53 | 0.93 |
C19—H19 | 0.93 | C54—C55 | 1.359 (5) |
C20—N5 | 1.320 (4) | C54—H54 | 0.93 |
C20—C21 | 1.401 (5) | C55—C57 | 1.425 (6) |
C20—H20 | 0.93 | C55—C56 | 1.499 (5) |
C21—C22 | 1.365 (4) | C56—O7 | 1.223 (6) |
C21—H21 | 0.93 | C56—O8 | 1.280 (5) |
C22—C23 | 1.399 (4) | C57—C58 | 1.422 (5) |
C22—H22 | 0.93 | C57—C62 | 1.425 (5) |
C23—C24 | 1.414 (4) | C58—C59 | 1.344 (7) |
C23—C31 | 1.424 (4) | C58—H58 | 0.93 |
C24—N5 | 1.354 (4) | C59—C60 | 1.406 (6) |
C24—C25 | 1.449 (4) | C59—H59 | 0.9300 |
C25—N6 | 1.355 (4) | C60—C61 | 1.352 (5) |
C25—C29 | 1.410 (4) | C60—H60 | 0.93 |
C26—N6 | 1.326 (4) | C61—C62 | 1.413 (5) |
C26—C27 | 1.382 (5) | C61—H61 | 0.93 |
C26—H26 | 0.93 | Zn1—N1 | 2.100 (3) |
C27—C28 | 1.375 (5) | Zn1—N2 | 2.092 (3) |
C27—H27 | 0.93 | N3—H3 | 0.86 |
C28—C29 | 1.393 (5) | Zn1—N5 | 2.115 (3) |
C28—H28 | 0.93 | Zn1—N6 | 2.121 (3) |
C29—C30 | 1.438 (4) | N8—H8B | 0.86 |
C30—N7 | 1.377 (4) | Zn1—O1 | 2.033 (3) |
C30—C31 | 1.378 (4) | O4—H4 | 0.82 |
C31—N8 | 1.371 (4) | O8—H8 | 0.82 |
C32—C33 | 1.381 (5) | O9—H9 | 0.82 |
C32—C37 | 1.393 (4) | O10—H10 | 0.82 |
C32—C38 | 1.466 (4) | O1W—HW11 | 0.90 (5) |
C33—C34 | 1.382 (4) | O1W—HW12 | 0.91 (6) |
C33—H33 | 0.93 | O2W—HW21 | 0.89 (6) |
C34—C35 | 1.386 (4) | O2W—HW22 | 0.90 (5) |
C34—H34 | 0.93 | | |
| | | |
N1—C1—C2 | 122.8 (3) | N7—C38—C32 | 126.5 (3) |
N1—C1—H1 | 118.6 | N8—C38—C32 | 121.6 (3) |
C2—C1—H1 | 118.6 | O2—C39—O1 | 124.0 (3) |
C3—C2—C1 | 119.2 (3) | O2—C39—C40 | 119.3 (3) |
C3—C2—H2 | 120.4 | O1—C39—C40 | 116.6 (3) |
C1—C2—H2 | 120.4 | C41—C40—C50 | 119.9 (3) |
C2—C3—C4 | 119.4 (3) | C41—C40—C39 | 117.4 (3) |
C2—C3—H3A | 120.3 | C50—C40—C39 | 122.6 (3) |
C4—C3—H3A | 120.3 | C40—C41—C42 | 121.1 (3) |
C3—C4—C5 | 118.0 (3) | C40—C41—H41 | 119.4 |
C3—C4—C12 | 126.6 (3) | C42—C41—H41 | 119.4 |
C5—C4—C12 | 115.3 (3) | C43—C42—C41 | 121.5 (3) |
N1—C5—C4 | 121.7 (3) | C43—C42—H42 | 119.3 |
N1—C5—C6 | 116.3 (3) | C41—C42—H42 | 119.3 |
C4—C5—C6 | 122.0 (3) | C42—C43—C45 | 119.0 (3) |
N2—C6—C7 | 121.3 (3) | C42—C43—C44 | 117.4 (3) |
N2—C6—C5 | 117.8 (3) | C45—C43—C44 | 123.6 (3) |
C7—C6—C5 | 120.9 (3) | O3—C44—O4 | 122.3 (4) |
C8—C7—C6 | 118.1 (3) | O3—C44—C43 | 125.6 (3) |
C8—C7—C11 | 125.5 (3) | O4—C44—C43 | 112.1 (3) |
C6—C7—C11 | 116.4 (3) | C50—C45—C46 | 117.5 (3) |
C9—C8—C7 | 119.5 (3) | C50—C45—C43 | 119.3 (3) |
C9—C8—H8A | 120.3 | C46—C45—C43 | 123.1 (3) |
C7—C8—H8A | 120.3 | C47—C46—C45 | 121.4 (3) |
C8—C9—C10 | 119.2 (3) | C47—C46—H46 | 119.3 |
C8—C9—H9A | 120.4 | C45—C46—H46 | 119.3 |
C10—C9—H9A | 120.4 | C46—C47—C48 | 120.2 (3) |
N2—C10—C9 | 122.8 (3) | C46—C47—H47 | 119.9 |
N2—C10—H10A | 118.6 | C48—C47—H47 | 119.9 |
C9—C10—H10A | 118.6 | C49—C48—C47 | 120.6 (3) |
N4—C11—C12 | 111.4 (3) | C49—C48—H48 | 119.7 |
N4—C11—C7 | 127.4 (3) | C47—C48—H48 | 119.7 |
C12—C11—C7 | 121.3 (3) | C48—C49—C50 | 120.8 (3) |
N3—C12—C11 | 105.7 (3) | C48—C49—H49 | 119.6 |
N3—C12—C4 | 130.2 (3) | C50—C49—H49 | 119.6 |
C11—C12—C4 | 124.1 (3) | C49—C50—C45 | 119.3 (3) |
N4—C13—N3 | 112.4 (3) | C49—C50—C40 | 121.6 (3) |
N4—C13—C14 | 124.2 (3) | C45—C50—C40 | 119.0 (3) |
N3—C13—C14 | 123.3 (3) | O5—C51—O6 | 125.0 (3) |
C15—C14—C19 | 118.5 (3) | O5—C51—C52 | 117.9 (3) |
C15—C14—C13 | 118.6 (3) | O6—C51—C52 | 117.1 (3) |
C19—C14—C13 | 122.9 (3) | C53—C52—C62 | 120.3 (3) |
C14—C15—C16 | 121.1 (3) | C53—C52—C51 | 120.0 (3) |
C14—C15—H15 | 119.4 | C62—C52—C51 | 119.7 (3) |
C16—C15—H15 | 119.4 | C52—C53—C54 | 120.5 (4) |
C17—C16—C15 | 119.9 (4) | C52—C53—H53 | 119.8 |
C17—C16—H16 | 120.0 | C54—C53—H53 | 119.8 |
C15—C16—H16 | 120.0 | C55—C54—C53 | 120.8 (4) |
O10—C17—C18 | 118.2 (3) | C55—C54—H54 | 119.6 |
O10—C17—C16 | 122.5 (3) | C53—C54—H54 | 119.6 |
C18—C17—C16 | 119.3 (3) | C54—C55—C57 | 120.4 (3) |
C17—C18—C19 | 120.6 (4) | C54—C55—C56 | 114.8 (4) |
C17—C18—H18 | 119.7 | C57—C55—C56 | 124.8 (4) |
C19—C18—H18 | 119.7 | O7—C56—O8 | 120.8 (4) |
C18—C19—C14 | 120.5 (4) | O7—C56—C55 | 122.1 (4) |
C18—C19—H19 | 119.8 | O8—C56—C55 | 116.6 (4) |
C14—C19—H19 | 119.8 | C58—C57—C62 | 117.3 (4) |
N5—C20—C21 | 123.4 (3) | C58—C57—C55 | 124.0 (3) |
N5—C20—H20 | 118.3 | C62—C57—C55 | 118.7 (3) |
C21—C20—H20 | 118.3 | C59—C58—C57 | 121.9 (4) |
C22—C21—C20 | 118.7 (3) | C59—C58—H58 | 119.0 |
C22—C21—H21 | 120.7 | C57—C58—H58 | 119.0 |
C20—C21—H21 | 120.7 | C58—C59—C60 | 120.8 (4) |
C21—C22—C23 | 119.5 (3) | C58—C59—H59 | 119.6 |
C21—C22—H22 | 120.2 | C60—C59—H59 | 119.6 |
C23—C22—H22 | 120.2 | C61—C60—C59 | 119.3 (4) |
C22—C23—C24 | 118.2 (3) | C61—C60—H60 | 120.4 |
C22—C23—C31 | 126.2 (3) | C59—C60—H60 | 120.4 |
C24—C23—C31 | 115.6 (3) | C60—C61—C62 | 122.0 (4) |
N5—C24—C23 | 121.5 (3) | C60—C61—H61 | 119.0 |
N5—C24—C25 | 117.4 (3) | C62—C61—H61 | 119.0 |
C23—C24—C25 | 121.1 (3) | C61—C62—C52 | 122.0 (3) |
N6—C25—C29 | 121.7 (3) | C61—C62—C57 | 118.7 (3) |
N6—C25—C24 | 116.7 (3) | C52—C62—C57 | 119.3 (3) |
C29—C25—C24 | 121.5 (3) | C1—N1—C5 | 118.9 (3) |
N6—C26—C27 | 123.5 (3) | C1—N1—Zn1 | 127.4 (2) |
N6—C26—H26 | 118.2 | C5—N1—Zn1 | 113.7 (2) |
C27—C26—H26 | 118.2 | C10—N2—C6 | 119.1 (3) |
C28—C27—C26 | 118.7 (3) | C10—N2—Zn1 | 128.2 (2) |
C28—C27—H27 | 120.6 | C6—N2—Zn1 | 112.7 (2) |
C26—C27—H27 | 120.6 | C13—N3—C12 | 106.5 (3) |
C27—C28—C29 | 119.6 (3) | C13—N3—H3 | 126.8 |
C27—C28—H28 | 120.2 | C12—N3—H3 | 126.8 |
C29—C28—H28 | 120.2 | C13—N4—C11 | 103.9 (3) |
C28—C29—C25 | 118.0 (3) | C20—N5—C24 | 118.7 (3) |
C28—C29—C30 | 125.2 (3) | C20—N5—Zn1 | 127.9 (2) |
C25—C29—C30 | 116.7 (3) | C24—N5—Zn1 | 112.8 (2) |
N7—C30—C31 | 110.4 (3) | C26—N6—C25 | 118.4 (3) |
N7—C30—C29 | 128.8 (3) | C26—N6—Zn1 | 127.5 (2) |
C31—C30—C29 | 120.7 (3) | C25—N6—Zn1 | 113.1 (2) |
N8—C31—C30 | 106.1 (3) | C38—N7—C30 | 105.0 (2) |
N8—C31—C23 | 129.7 (3) | C31—N8—C38 | 106.6 (3) |
C30—C31—C23 | 124.2 (3) | C31—N8—H8B | 126.7 |
C33—C32—C37 | 118.4 (3) | C38—N8—H8B | 126.7 |
C33—C32—C38 | 121.7 (3) | C39—O1—Zn1 | 106.2 (2) |
C37—C32—C38 | 119.9 (3) | C44—O4—H4 | 109.5 |
C32—C33—C34 | 121.0 (3) | C56—O8—H8 | 109.5 |
C32—C33—H33 | 119.5 | C35—O9—H9 | 109.5 |
C34—C33—H33 | 119.5 | C17—O10—H10 | 109.5 |
C33—C34—C35 | 119.8 (3) | O1—Zn1—N2 | 134.47 (11) |
C33—C34—H34 | 120.1 | O1—Zn1—N1 | 89.68 (10) |
C35—C34—H34 | 120.1 | N2—Zn1—N1 | 79.47 (10) |
O9—C35—C36 | 122.5 (3) | O1—Zn1—N5 | 100.93 (11) |
O9—C35—C34 | 117.4 (3) | N2—Zn1—N5 | 124.19 (10) |
C36—C35—C34 | 120.1 (3) | N1—Zn1—N5 | 97.57 (10) |
C35—C36—C37 | 119.4 (3) | O1—Zn1—N6 | 90.44 (11) |
C35—C36—H36 | 120.3 | N2—Zn1—N6 | 103.14 (10) |
C37—C36—H36 | 120.3 | N1—Zn1—N6 | 176.13 (10) |
C36—C37—C32 | 121.2 (3) | N5—Zn1—N6 | 78.61 (10) |
C36—C37—H37 | 119.4 | HW11—O1W—HW12 | 113 (6) |
C32—C37—H37 | 119.4 | HW21—O2W—HW22 | 122 (5) |
N7—C38—N8 | 111.9 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—HW11···N7 | 0.91 (6) | 2.04 (4) | 2.869 (4) | 152 (6) |
O1W—HW12···N4i | 0.92 (5) | 2.00 (5) | 2.899 (4) | 168 (5) |
O2W—HW22···O6ii | 0.90 (5) | 1.95 (5) | 2.831 (4) | 166 (6) |
O2W—HW21···O8iii | 0.89 (6) | 2.12 (5) | 2.999 (5) | 167 (5) |
O9—H9···O5iv | 0.82 | 1.84 | 2.560 (3) | 146 |
O10—H10···O9v | 0.82 | 1.93 | 2.721 (4) | 162 |
O8—H8···O1Wvi | 0.82 | 1.82 | 2.625 (4) | 168 |
O4—H4···O6ii | 0.82 | 1.86 | 2.497 (4) | 134 |
N8—H8B···O2i | 0.86 | 2.06 | 2.809 (4) | 145 |
N3—H3···O2Wvii | 0.86 | 1.99 | 2.810 (4) | 160 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x−1, y, z; (iii) x−1/2, −y+1/2, z+1/2; (iv) −x+2, −y, −z+1; (v) x, y+1, z−1; (vi) x, y, z−1; (vii) x+1/2, −y+1/2, z−1/2. |