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In the title compound, [Zn(C12H7O4)(C19H12N4O)2](C12H7O4)·2H2O or [Zn(L)2(HNDC)](HNDC)·2H2O, where HNDC is the naphthalene-1,4-dicarboxyl­ate monoanion and L is 4-(1H-1,3,7,8-tetra­azacyclo­penta­[l]phenanthren-2-yl)­phenol, the ZnII 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806042656/ci2188sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806042656/ci2188Isup2.hkl
Contains datablock I

CCDC reference: 627460

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](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

Computing details top

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-(1H-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)·2H2OF(000) = 2384
Mr = 1156.41Dx = 1.516 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 30831 reflections
a = 17.141 (3) Åθ = 3.0–27.5°
b = 16.729 (3) ŵ = 0.56 mm1
c = 19.595 (4) ÅT = 292 K
β = 115.60 (3)°Block, yellow
V = 5067 (2) Å30.30 × 0.27 × 0.24 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
11528 independent reflections
Radiation source: rotorating anode7908 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.070
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = 2222
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 2121
Tmin = 0.840, Tmax = 0.881l = 2525
48539 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062Hydrogen site location: constr
wR(F2) = 0.163H 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 parametersΔρmax = 2.10 e Å3
4 restraintsΔρmin = 0.48 e Å3
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
xyzUiso*/Ueq
C10.7137 (2)0.1373 (2)0.01021 (19)0.0408 (8)
H10.69460.09210.02620.049*
C20.7123 (3)0.1367 (2)0.0611 (2)0.0464 (9)
H20.69370.09160.09160.056*
C30.7383 (2)0.2031 (2)0.08582 (19)0.0402 (8)
H3A0.73680.20400.13380.048*
C40.7671 (2)0.26969 (19)0.03858 (17)0.0330 (7)
C50.7681 (2)0.26520 (18)0.03321 (17)0.0310 (6)
C60.79748 (19)0.33113 (19)0.08639 (16)0.0308 (6)
C70.8265 (2)0.40297 (19)0.06760 (18)0.0359 (7)
C80.8520 (2)0.4646 (2)0.1204 (2)0.0430 (8)
H8A0.87070.51310.10940.052*
C90.8494 (2)0.4534 (2)0.1887 (2)0.0457 (8)
H9A0.86620.49410.22450.055*
C100.8215 (2)0.3806 (2)0.20377 (19)0.0402 (8)
H10A0.82100.37320.25060.048*
C110.8270 (2)0.40587 (19)0.00556 (18)0.0355 (7)
C120.7986 (2)0.34231 (19)0.05466 (18)0.0349 (7)
C130.8424 (2)0.4406 (2)0.10367 (19)0.0418 (8)
C140.8672 (2)0.4842 (2)0.1557 (2)0.0426 (8)
C150.9119 (3)0.5550 (2)0.1318 (2)0.0516 (10)
H150.92270.57500.08420.062*
C160.9408 (3)0.5967 (2)0.1771 (2)0.0523 (10)
H160.96980.64500.16050.063*
C170.9267 (2)0.5668 (2)0.24702 (19)0.0434 (8)
C180.8815 (3)0.4966 (2)0.2717 (2)0.0548 (10)
H180.87120.47640.31900.066*
C190.8513 (3)0.4558 (2)0.2268 (2)0.0551 (10)
H190.82010.40870.24450.066*
C200.8612 (2)0.0587 (2)0.18020 (17)0.0353 (7)
H200.85850.07310.13340.042*
C210.9000 (2)0.0143 (2)0.21184 (18)0.0391 (7)
H210.92160.04780.18620.047*
C220.9053 (2)0.0354 (2)0.28104 (18)0.0365 (7)
H220.93030.08380.30300.044*
C230.8729 (2)0.01632 (18)0.31873 (16)0.0304 (6)
C240.83434 (19)0.08871 (18)0.28267 (15)0.0292 (6)
C250.7995 (2)0.14502 (18)0.31853 (16)0.0298 (6)
C260.7237 (2)0.2617 (2)0.30748 (19)0.0420 (8)
H260.69660.30680.27950.050*
C270.7232 (3)0.2510 (2)0.3772 (2)0.0451 (8)
H270.69560.28760.39510.054*
C280.7642 (2)0.1852 (2)0.41958 (19)0.0414 (8)
H280.76570.17730.46710.050*
C290.8036 (2)0.13036 (18)0.39085 (17)0.0322 (7)
C300.8453 (2)0.05765 (19)0.42772 (16)0.0318 (7)
C310.8753 (2)0.00364 (18)0.39148 (16)0.0315 (6)
C320.9205 (2)0.09796 (18)0.56673 (16)0.0318 (6)
C330.9627 (2)0.1687 (2)0.56822 (18)0.0384 (7)
H330.97170.18330.52640.046*
C340.9919 (2)0.2181 (2)0.63088 (18)0.0398 (8)
H341.01990.26570.63090.048*
C350.9792 (2)0.19646 (19)0.69365 (17)0.0345 (7)
C360.9354 (2)0.1267 (2)0.69280 (17)0.0367 (7)
H360.92530.11290.73420.044*
C370.9070 (2)0.0778 (2)0.62981 (17)0.0368 (7)
H370.87830.03050.62950.044*
C380.8938 (2)0.04264 (19)0.50257 (16)0.0316 (6)
C390.5774 (2)0.2170 (2)0.11505 (17)0.0391 (8)
C400.4832 (2)0.1959 (2)0.08709 (19)0.0382 (7)
C410.4406 (3)0.2260 (2)0.1260 (2)0.0531 (10)
H410.46790.26360.16400.064*
C420.3568 (3)0.2016 (2)0.1101 (2)0.0504 (9)
H420.33010.22170.13890.060*
C430.3129 (2)0.1486 (2)0.05287 (19)0.0387 (7)
C440.2235 (2)0.1263 (2)0.0403 (2)0.0459 (8)
C450.3535 (2)0.11956 (19)0.00755 (17)0.0341 (7)
C460.3114 (2)0.0682 (2)0.05575 (19)0.0416 (8)
H460.25510.05130.06810.050*
C470.3518 (3)0.0430 (2)0.0989 (2)0.0461 (9)
H470.32280.00970.14020.055*
C480.4359 (3)0.0668 (2)0.0810 (2)0.0462 (9)
H480.46290.04940.11050.055*
C490.4794 (2)0.1156 (2)0.02063 (18)0.0403 (8)
H490.53570.13130.00960.048*
C500.4399 (2)0.14277 (19)0.02540 (17)0.0336 (7)
C511.0030 (2)0.1676 (2)0.08843 (18)0.0372 (7)
C520.9672 (2)0.1505 (2)0.00451 (18)0.0374 (7)
C530.9249 (3)0.0801 (2)0.0238 (2)0.0486 (9)
H530.91700.04360.00840.058*
C540.8933 (3)0.0625 (2)0.1017 (2)0.0532 (10)
H540.86590.01390.12000.064*
C550.9025 (2)0.1156 (2)0.15019 (19)0.0471 (9)
C560.8649 (3)0.0891 (3)0.2312 (2)0.0630 (12)
C570.9469 (2)0.1892 (2)0.12275 (19)0.0452 (8)
C580.9635 (3)0.2460 (3)0.1688 (2)0.0585 (11)
H580.94350.23590.22030.070*
C591.0073 (3)0.3139 (3)0.1402 (3)0.0710 (13)
H591.01750.34950.17190.085*
C601.0380 (3)0.3319 (3)0.0628 (2)0.0677 (12)
H601.06740.37940.04350.081*
C611.0243 (3)0.2792 (2)0.0167 (2)0.0534 (10)
H611.04450.29140.03440.064*
C620.9802 (2)0.2063 (2)0.04393 (18)0.0405 (8)
N10.74122 (17)0.19933 (16)0.05644 (15)0.0347 (6)
N20.79574 (17)0.32137 (16)0.15451 (14)0.0339 (6)
N30.80802 (19)0.36529 (16)0.11782 (15)0.0384 (6)
H30.79490.33780.15840.046*
N40.8541 (2)0.46778 (17)0.03590 (16)0.0410 (7)
N50.82815 (17)0.10803 (15)0.21339 (13)0.0316 (6)
N60.76086 (18)0.21123 (15)0.27834 (14)0.0347 (6)
N70.85796 (17)0.02881 (16)0.49755 (14)0.0334 (6)
N80.90563 (17)0.06056 (16)0.43926 (14)0.0342 (6)
H8B0.92770.10360.43120.041*
O10.62927 (16)0.15975 (17)0.12892 (14)0.0483 (6)
O20.59966 (18)0.28844 (16)0.12537 (14)0.0521 (7)
O30.1677 (2)0.1013 (3)0.0181 (2)0.0956 (13)
O40.2103 (2)0.1395 (3)0.09875 (18)0.1012 (15)
H40.16070.12660.08980.152*
O50.95177 (17)0.18772 (18)0.11392 (14)0.0552 (7)
O61.08248 (17)0.1607 (2)0.12627 (14)0.0644 (8)
O70.8632 (3)0.0188 (2)0.2489 (2)0.1145 (16)
O80.8252 (2)0.1422 (2)0.28120 (16)0.0798 (10)
H80.80700.12220.32350.120*
O91.01236 (17)0.24543 (15)0.75489 (13)0.0453 (6)
H91.00210.22680.78890.068*
O100.95701 (18)0.60334 (17)0.29258 (14)0.0545 (7)
H100.98340.64390.27180.082*
Zn10.74898 (2)0.20909 (2)0.16604 (2)0.03441 (12)
O1W0.7679 (2)0.09929 (17)0.57649 (15)0.0526 (7)
O2W0.2255 (2)0.2271 (2)0.25048 (16)0.0633 (8)
HW110.812 (3)0.082 (4)0.566 (4)0.14 (3)*
HW120.725 (3)0.062 (3)0.566 (3)0.11 (2)*
HW210.260 (3)0.260 (3)0.240 (3)0.10 (2)*
HW220.175 (2)0.210 (3)0.214 (3)0.11 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.046 (2)0.0369 (18)0.0380 (17)0.0055 (15)0.0163 (15)0.0062 (15)
C20.058 (2)0.0371 (19)0.0379 (18)0.0077 (16)0.0150 (17)0.0033 (15)
C30.048 (2)0.0405 (18)0.0319 (16)0.0048 (16)0.0173 (15)0.0007 (14)
C40.0309 (16)0.0350 (16)0.0311 (15)0.0033 (13)0.0116 (13)0.0073 (13)
C50.0292 (15)0.0326 (16)0.0285 (14)0.0023 (12)0.0100 (12)0.0076 (13)
C60.0303 (15)0.0340 (16)0.0270 (14)0.0037 (13)0.0113 (12)0.0076 (13)
C70.0387 (18)0.0350 (17)0.0331 (16)0.0016 (14)0.0147 (14)0.0065 (14)
C80.053 (2)0.0333 (17)0.0442 (19)0.0062 (15)0.0228 (17)0.0007 (15)
C90.054 (2)0.044 (2)0.0416 (19)0.0056 (17)0.0222 (17)0.0057 (16)
C100.0438 (19)0.0438 (19)0.0339 (16)0.0010 (15)0.0176 (15)0.0004 (15)
C110.0400 (18)0.0343 (16)0.0347 (16)0.0005 (14)0.0184 (14)0.0046 (14)
C120.0364 (17)0.0363 (17)0.0332 (16)0.0005 (14)0.0161 (14)0.0066 (14)
C130.050 (2)0.0381 (18)0.0404 (18)0.0030 (15)0.0228 (16)0.0062 (15)
C140.050 (2)0.0410 (19)0.0406 (18)0.0036 (16)0.0228 (16)0.0075 (15)
C150.070 (3)0.050 (2)0.043 (2)0.0140 (19)0.0336 (19)0.0034 (17)
C160.068 (3)0.049 (2)0.047 (2)0.0156 (19)0.032 (2)0.0019 (18)
C170.051 (2)0.046 (2)0.0360 (17)0.0022 (16)0.0208 (16)0.0100 (15)
C180.078 (3)0.050 (2)0.0384 (19)0.011 (2)0.0270 (19)0.0037 (17)
C190.078 (3)0.048 (2)0.0385 (19)0.018 (2)0.0243 (19)0.0001 (17)
C200.0360 (17)0.0459 (19)0.0235 (14)0.0042 (14)0.0123 (13)0.0040 (13)
C210.0427 (19)0.0457 (19)0.0319 (16)0.0059 (15)0.0189 (15)0.0008 (15)
C220.0388 (18)0.0360 (17)0.0340 (16)0.0032 (14)0.0150 (14)0.0018 (14)
C230.0317 (16)0.0326 (16)0.0240 (14)0.0020 (12)0.0092 (12)0.0006 (12)
C240.0315 (15)0.0303 (15)0.0232 (13)0.0053 (12)0.0094 (12)0.0020 (12)
C250.0324 (16)0.0289 (15)0.0245 (14)0.0037 (12)0.0091 (12)0.0012 (12)
C260.056 (2)0.0314 (17)0.0366 (17)0.0063 (15)0.0186 (16)0.0045 (14)
C270.061 (2)0.0393 (18)0.0397 (18)0.0080 (17)0.0256 (18)0.0021 (16)
C280.059 (2)0.0373 (18)0.0307 (16)0.0022 (16)0.0216 (16)0.0014 (14)
C290.0404 (17)0.0284 (15)0.0268 (14)0.0018 (13)0.0136 (13)0.0001 (12)
C300.0358 (17)0.0346 (16)0.0239 (14)0.0016 (13)0.0119 (13)0.0022 (12)
C310.0391 (17)0.0290 (15)0.0249 (14)0.0005 (13)0.0126 (13)0.0048 (12)
C320.0362 (16)0.0343 (16)0.0227 (13)0.0046 (13)0.0107 (12)0.0022 (12)
C330.051 (2)0.0378 (18)0.0283 (15)0.0005 (15)0.0188 (15)0.0002 (14)
C340.051 (2)0.0353 (17)0.0311 (16)0.0046 (15)0.0158 (15)0.0039 (14)
C350.0379 (17)0.0352 (17)0.0265 (14)0.0055 (13)0.0103 (13)0.0038 (13)
C360.0414 (18)0.0443 (19)0.0266 (15)0.0011 (15)0.0168 (14)0.0018 (14)
C370.0421 (18)0.0383 (17)0.0308 (15)0.0027 (14)0.0165 (14)0.0040 (14)
C380.0355 (16)0.0334 (16)0.0237 (14)0.0053 (13)0.0107 (12)0.0017 (12)
C390.0408 (18)0.051 (2)0.0253 (15)0.0116 (17)0.0145 (14)0.0055 (15)
C400.0374 (18)0.0425 (19)0.0351 (16)0.0060 (14)0.0162 (14)0.0055 (14)
C410.051 (2)0.062 (2)0.051 (2)0.0183 (19)0.0263 (18)0.0272 (19)
C420.051 (2)0.062 (2)0.049 (2)0.0042 (18)0.0309 (18)0.0132 (19)
C430.0341 (17)0.0459 (19)0.0374 (17)0.0015 (14)0.0166 (14)0.0019 (15)
C440.0384 (19)0.059 (2)0.0434 (19)0.0000 (17)0.0206 (17)0.0059 (18)
C450.0363 (17)0.0322 (16)0.0324 (15)0.0018 (13)0.0137 (13)0.0050 (13)
C460.0410 (19)0.0378 (18)0.0418 (18)0.0093 (15)0.0140 (15)0.0038 (15)
C470.056 (2)0.0374 (18)0.0431 (19)0.0085 (16)0.0200 (17)0.0101 (16)
C480.060 (2)0.048 (2)0.0380 (18)0.0016 (18)0.0281 (17)0.0059 (16)
C490.0425 (19)0.0459 (19)0.0362 (17)0.0031 (15)0.0204 (15)0.0012 (15)
C500.0371 (17)0.0318 (16)0.0325 (15)0.0018 (13)0.0155 (14)0.0025 (13)
C510.0357 (18)0.0468 (19)0.0319 (16)0.0008 (15)0.0173 (14)0.0057 (15)
C520.0328 (17)0.0480 (19)0.0310 (16)0.0003 (14)0.0134 (14)0.0006 (15)
C530.054 (2)0.052 (2)0.0428 (19)0.0058 (18)0.0230 (17)0.0010 (17)
C540.057 (2)0.050 (2)0.048 (2)0.0032 (18)0.0178 (19)0.0081 (18)
C550.048 (2)0.056 (2)0.0340 (17)0.0084 (18)0.0145 (16)0.0069 (17)
C560.077 (3)0.066 (3)0.042 (2)0.022 (2)0.022 (2)0.008 (2)
C570.047 (2)0.058 (2)0.0324 (17)0.0091 (17)0.0191 (16)0.0062 (16)
C580.068 (3)0.076 (3)0.0357 (19)0.003 (2)0.0261 (19)0.009 (2)
C590.079 (3)0.086 (3)0.054 (2)0.011 (3)0.034 (2)0.025 (2)
C600.076 (3)0.069 (3)0.054 (2)0.020 (2)0.025 (2)0.006 (2)
C610.060 (2)0.062 (3)0.0347 (18)0.014 (2)0.0171 (18)0.0013 (17)
C620.0400 (18)0.053 (2)0.0286 (15)0.0016 (16)0.0146 (14)0.0030 (15)
N10.0353 (14)0.0350 (14)0.0315 (13)0.0029 (11)0.0123 (11)0.0064 (12)
N20.0332 (14)0.0368 (14)0.0282 (13)0.0001 (11)0.0099 (11)0.0053 (11)
N30.0477 (17)0.0382 (15)0.0339 (14)0.0023 (13)0.0219 (13)0.0053 (12)
N40.0540 (18)0.0373 (15)0.0384 (15)0.0058 (13)0.0262 (14)0.0036 (12)
N50.0342 (14)0.0350 (14)0.0245 (12)0.0042 (11)0.0118 (11)0.0041 (11)
N60.0415 (15)0.0325 (14)0.0271 (12)0.0003 (12)0.0120 (11)0.0027 (11)
N70.0422 (15)0.0351 (14)0.0239 (12)0.0005 (12)0.0153 (11)0.0019 (11)
N80.0429 (15)0.0327 (14)0.0271 (12)0.0034 (12)0.0151 (12)0.0054 (11)
O10.0387 (14)0.0594 (16)0.0454 (14)0.0042 (12)0.0168 (11)0.0071 (12)
O20.0542 (16)0.0525 (16)0.0431 (14)0.0184 (13)0.0150 (12)0.0015 (12)
O30.061 (2)0.152 (4)0.088 (3)0.042 (2)0.046 (2)0.048 (3)
O40.0425 (18)0.209 (5)0.0606 (19)0.021 (2)0.0305 (16)0.028 (2)
O50.0448 (15)0.089 (2)0.0346 (13)0.0104 (14)0.0197 (12)0.0050 (13)
O60.0353 (14)0.122 (3)0.0340 (13)0.0005 (15)0.0127 (11)0.0053 (15)
O70.180 (5)0.081 (3)0.065 (2)0.033 (3)0.036 (3)0.017 (2)
O80.110 (3)0.076 (2)0.0348 (14)0.019 (2)0.0144 (16)0.0083 (15)
O90.0653 (17)0.0428 (13)0.0297 (11)0.0096 (12)0.0224 (12)0.0113 (10)
O100.0671 (18)0.0601 (17)0.0417 (14)0.0127 (14)0.0286 (13)0.0085 (12)
Zn10.0381 (2)0.0357 (2)0.02697 (19)0.00311 (16)0.01175 (15)0.00712 (15)
O1W0.069 (2)0.0536 (16)0.0360 (13)0.0001 (15)0.0234 (14)0.0022 (12)
O2W0.073 (2)0.066 (2)0.0404 (15)0.0039 (17)0.0153 (15)0.0024 (14)
Geometric parameters (Å, º) top
C1—N11.323 (4)C35—O91.358 (4)
C1—C21.386 (5)C35—C361.383 (5)
C1—H10.93C36—C371.383 (4)
C2—C31.361 (5)C36—H360.93
C2—H20.93C37—H370.93
C3—C41.396 (5)C38—N71.328 (4)
C3—H3A0.93C38—N81.374 (4)
C4—C51.402 (4)C39—O21.244 (4)
C4—C121.419 (4)C39—O11.254 (4)
C5—N11.347 (4)C39—C401.506 (5)
C5—C61.450 (4)C40—C411.361 (5)
C6—N21.358 (4)C40—C501.424 (4)
C6—C71.409 (4)C41—C421.392 (5)
C7—C81.390 (5)C41—H410.93
C7—C111.438 (4)C42—C431.372 (5)
C8—C91.372 (5)C42—H420.93
C8—H8A0.93C43—C451.430 (4)
C9—C101.385 (5)C43—C441.490 (5)
C9—H9A0.93C44—O31.205 (5)
C10—N21.319 (4)C44—O41.280 (5)
C10—H10A0.93C45—C501.421 (4)
C11—N41.371 (4)C45—C461.423 (5)
C11—C121.374 (5)C46—C471.371 (5)
C12—N31.370 (4)C46—H460.93
C13—N41.334 (4)C47—C481.387 (5)
C13—N31.368 (4)C47—H470.93
C13—C141.458 (4)C48—C491.364 (5)
C14—C151.378 (5)C48—H480.9300
C14—C191.384 (5)C49—C501.416 (4)
C15—C161.380 (5)C49—H490.93
C15—H150.93C51—O51.230 (4)
C16—C171.378 (5)C51—O61.244 (4)
C16—H160.93C51—C521.514 (4)
C17—O101.357 (4)C52—C531.367 (5)
C17—C181.375 (5)C52—C621.416 (5)
C18—C191.377 (5)C53—C541.412 (5)
C18—H180.93C53—H530.93
C19—H190.93C54—C551.359 (5)
C20—N51.320 (4)C54—H540.93
C20—C211.401 (5)C55—C571.425 (6)
C20—H200.93C55—C561.499 (5)
C21—C221.365 (4)C56—O71.223 (6)
C21—H210.93C56—O81.280 (5)
C22—C231.399 (4)C57—C581.422 (5)
C22—H220.93C57—C621.425 (5)
C23—C241.414 (4)C58—C591.344 (7)
C23—C311.424 (4)C58—H580.93
C24—N51.354 (4)C59—C601.406 (6)
C24—C251.449 (4)C59—H590.9300
C25—N61.355 (4)C60—C611.352 (5)
C25—C291.410 (4)C60—H600.93
C26—N61.326 (4)C61—C621.413 (5)
C26—C271.382 (5)C61—H610.93
C26—H260.93Zn1—N12.100 (3)
C27—C281.375 (5)Zn1—N22.092 (3)
C27—H270.93N3—H30.86
C28—C291.393 (5)Zn1—N52.115 (3)
C28—H280.93Zn1—N62.121 (3)
C29—C301.438 (4)N8—H8B0.86
C30—N71.377 (4)Zn1—O12.033 (3)
C30—C311.378 (4)O4—H40.82
C31—N81.371 (4)O8—H80.82
C32—C331.381 (5)O9—H90.82
C32—C371.393 (4)O10—H100.82
C32—C381.466 (4)O1W—HW110.90 (5)
C33—C341.382 (4)O1W—HW120.91 (6)
C33—H330.93O2W—HW210.89 (6)
C34—C351.386 (4)O2W—HW220.90 (5)
C34—H340.93
N1—C1—C2122.8 (3)N7—C38—C32126.5 (3)
N1—C1—H1118.6N8—C38—C32121.6 (3)
C2—C1—H1118.6O2—C39—O1124.0 (3)
C3—C2—C1119.2 (3)O2—C39—C40119.3 (3)
C3—C2—H2120.4O1—C39—C40116.6 (3)
C1—C2—H2120.4C41—C40—C50119.9 (3)
C2—C3—C4119.4 (3)C41—C40—C39117.4 (3)
C2—C3—H3A120.3C50—C40—C39122.6 (3)
C4—C3—H3A120.3C40—C41—C42121.1 (3)
C3—C4—C5118.0 (3)C40—C41—H41119.4
C3—C4—C12126.6 (3)C42—C41—H41119.4
C5—C4—C12115.3 (3)C43—C42—C41121.5 (3)
N1—C5—C4121.7 (3)C43—C42—H42119.3
N1—C5—C6116.3 (3)C41—C42—H42119.3
C4—C5—C6122.0 (3)C42—C43—C45119.0 (3)
N2—C6—C7121.3 (3)C42—C43—C44117.4 (3)
N2—C6—C5117.8 (3)C45—C43—C44123.6 (3)
C7—C6—C5120.9 (3)O3—C44—O4122.3 (4)
C8—C7—C6118.1 (3)O3—C44—C43125.6 (3)
C8—C7—C11125.5 (3)O4—C44—C43112.1 (3)
C6—C7—C11116.4 (3)C50—C45—C46117.5 (3)
C9—C8—C7119.5 (3)C50—C45—C43119.3 (3)
C9—C8—H8A120.3C46—C45—C43123.1 (3)
C7—C8—H8A120.3C47—C46—C45121.4 (3)
C8—C9—C10119.2 (3)C47—C46—H46119.3
C8—C9—H9A120.4C45—C46—H46119.3
C10—C9—H9A120.4C46—C47—C48120.2 (3)
N2—C10—C9122.8 (3)C46—C47—H47119.9
N2—C10—H10A118.6C48—C47—H47119.9
C9—C10—H10A118.6C49—C48—C47120.6 (3)
N4—C11—C12111.4 (3)C49—C48—H48119.7
N4—C11—C7127.4 (3)C47—C48—H48119.7
C12—C11—C7121.3 (3)C48—C49—C50120.8 (3)
N3—C12—C11105.7 (3)C48—C49—H49119.6
N3—C12—C4130.2 (3)C50—C49—H49119.6
C11—C12—C4124.1 (3)C49—C50—C45119.3 (3)
N4—C13—N3112.4 (3)C49—C50—C40121.6 (3)
N4—C13—C14124.2 (3)C45—C50—C40119.0 (3)
N3—C13—C14123.3 (3)O5—C51—O6125.0 (3)
C15—C14—C19118.5 (3)O5—C51—C52117.9 (3)
C15—C14—C13118.6 (3)O6—C51—C52117.1 (3)
C19—C14—C13122.9 (3)C53—C52—C62120.3 (3)
C14—C15—C16121.1 (3)C53—C52—C51120.0 (3)
C14—C15—H15119.4C62—C52—C51119.7 (3)
C16—C15—H15119.4C52—C53—C54120.5 (4)
C17—C16—C15119.9 (4)C52—C53—H53119.8
C17—C16—H16120.0C54—C53—H53119.8
C15—C16—H16120.0C55—C54—C53120.8 (4)
O10—C17—C18118.2 (3)C55—C54—H54119.6
O10—C17—C16122.5 (3)C53—C54—H54119.6
C18—C17—C16119.3 (3)C54—C55—C57120.4 (3)
C17—C18—C19120.6 (4)C54—C55—C56114.8 (4)
C17—C18—H18119.7C57—C55—C56124.8 (4)
C19—C18—H18119.7O7—C56—O8120.8 (4)
C18—C19—C14120.5 (4)O7—C56—C55122.1 (4)
C18—C19—H19119.8O8—C56—C55116.6 (4)
C14—C19—H19119.8C58—C57—C62117.3 (4)
N5—C20—C21123.4 (3)C58—C57—C55124.0 (3)
N5—C20—H20118.3C62—C57—C55118.7 (3)
C21—C20—H20118.3C59—C58—C57121.9 (4)
C22—C21—C20118.7 (3)C59—C58—H58119.0
C22—C21—H21120.7C57—C58—H58119.0
C20—C21—H21120.7C58—C59—C60120.8 (4)
C21—C22—C23119.5 (3)C58—C59—H59119.6
C21—C22—H22120.2C60—C59—H59119.6
C23—C22—H22120.2C61—C60—C59119.3 (4)
C22—C23—C24118.2 (3)C61—C60—H60120.4
C22—C23—C31126.2 (3)C59—C60—H60120.4
C24—C23—C31115.6 (3)C60—C61—C62122.0 (4)
N5—C24—C23121.5 (3)C60—C61—H61119.0
N5—C24—C25117.4 (3)C62—C61—H61119.0
C23—C24—C25121.1 (3)C61—C62—C52122.0 (3)
N6—C25—C29121.7 (3)C61—C62—C57118.7 (3)
N6—C25—C24116.7 (3)C52—C62—C57119.3 (3)
C29—C25—C24121.5 (3)C1—N1—C5118.9 (3)
N6—C26—C27123.5 (3)C1—N1—Zn1127.4 (2)
N6—C26—H26118.2C5—N1—Zn1113.7 (2)
C27—C26—H26118.2C10—N2—C6119.1 (3)
C28—C27—C26118.7 (3)C10—N2—Zn1128.2 (2)
C28—C27—H27120.6C6—N2—Zn1112.7 (2)
C26—C27—H27120.6C13—N3—C12106.5 (3)
C27—C28—C29119.6 (3)C13—N3—H3126.8
C27—C28—H28120.2C12—N3—H3126.8
C29—C28—H28120.2C13—N4—C11103.9 (3)
C28—C29—C25118.0 (3)C20—N5—C24118.7 (3)
C28—C29—C30125.2 (3)C20—N5—Zn1127.9 (2)
C25—C29—C30116.7 (3)C24—N5—Zn1112.8 (2)
N7—C30—C31110.4 (3)C26—N6—C25118.4 (3)
N7—C30—C29128.8 (3)C26—N6—Zn1127.5 (2)
C31—C30—C29120.7 (3)C25—N6—Zn1113.1 (2)
N8—C31—C30106.1 (3)C38—N7—C30105.0 (2)
N8—C31—C23129.7 (3)C31—N8—C38106.6 (3)
C30—C31—C23124.2 (3)C31—N8—H8B126.7
C33—C32—C37118.4 (3)C38—N8—H8B126.7
C33—C32—C38121.7 (3)C39—O1—Zn1106.2 (2)
C37—C32—C38119.9 (3)C44—O4—H4109.5
C32—C33—C34121.0 (3)C56—O8—H8109.5
C32—C33—H33119.5C35—O9—H9109.5
C34—C33—H33119.5C17—O10—H10109.5
C33—C34—C35119.8 (3)O1—Zn1—N2134.47 (11)
C33—C34—H34120.1O1—Zn1—N189.68 (10)
C35—C34—H34120.1N2—Zn1—N179.47 (10)
O9—C35—C36122.5 (3)O1—Zn1—N5100.93 (11)
O9—C35—C34117.4 (3)N2—Zn1—N5124.19 (10)
C36—C35—C34120.1 (3)N1—Zn1—N597.57 (10)
C35—C36—C37119.4 (3)O1—Zn1—N690.44 (11)
C35—C36—H36120.3N2—Zn1—N6103.14 (10)
C37—C36—H36120.3N1—Zn1—N6176.13 (10)
C36—C37—C32121.2 (3)N5—Zn1—N678.61 (10)
C36—C37—H37119.4HW11—O1W—HW12113 (6)
C32—C37—H37119.4HW21—O2W—HW22122 (5)
N7—C38—N8111.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—HW11···N70.91 (6)2.04 (4)2.869 (4)152 (6)
O1W—HW12···N4i0.92 (5)2.00 (5)2.899 (4)168 (5)
O2W—HW22···O6ii0.90 (5)1.95 (5)2.831 (4)166 (6)
O2W—HW21···O8iii0.89 (6)2.12 (5)2.999 (5)167 (5)
O9—H9···O5iv0.821.842.560 (3)146
O10—H10···O9v0.821.932.721 (4)162
O8—H8···O1Wvi0.821.822.625 (4)168
O4—H4···O6ii0.821.862.497 (4)134
N8—H8B···O2i0.862.062.809 (4)145
N3—H3···O2Wvii0.861.992.810 (4)160
Symmetry codes: (i) x+3/2, y1/2, z+1/2; (ii) x1, y, z; (iii) x1/2, y+1/2, z+1/2; (iv) x+2, y, z+1; (v) x, y+1, z1; (vi) x, y, z1; (vii) x+1/2, y+1/2, z1/2.
 

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