Bis(isoquinoline-1-carboxylato-[kappa]²O,N)(1,10-phenanthroline-[kappa]²N,N')zinc(II) dimethylformamide sesqui­solvate

The asymmetric unit of the title compound, [Zn(C₁₀H₆NO₂)₂(C₁₂H₈N₂)]·1.5C₃H₇NO, contains one monomeric zinc com­plex and 1.5 disordered di­methyl­form­amide solvate mol­ecules. The Zn atom is coordinated to one 1,10-phenanthroline ligand and to two iso­quinoline­carboxyl­ate anions (IQC^-) via their N and O atoms. The complex exhibits a distorted octahedral geometry around the Zn^II atom, with the apical positions occupied by the O atoms of the IQC^- ligands. The Zn atom lies 0.049 (1) Å out of the basal plane. The crystal packing is characterized by several hydrogen bonds.

Computing details

Data collection: IPDS Software (Stoe & Cie, 1996); cell refinement: IPDS Software; data reduction: X-RED (Stoe & Cie, 1996); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: WinGX (Farrugia, 1999).

Bis(isoquinoline-1-carboxylato-κ²O,N)(1,10-phenanthroline-κ²N,N')zinc(II) dimethylformamide sesquisolvate

Crystal data

[Zn(C10H6NO2)2(C12H8N2)]·1.5C3H7NO	F(000) = 1448
Mr = 699.55	Dx = 1.482 Mg m^−3 Dm = 1.47 Mg m^−3 Dm measured by flotation (CHCl3/CH2Cl2)
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8000 reflections
a = 17.077 (2) Å	θ = 2.1–26.1°
b = 12.747 (1) Å	µ = 0.84 mm^−1
c = 14.422 (1) Å	T = 170 K
β = 93.22 (1)°	Parallelepiped, colourless
V = 3134.2 (5) Å^3	0.40 × 0.25 × 0.20 mm
Z = 4

Data collection

Stoe IPDS diffractometer	5303 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
Graphite monochromator	θmax = 26.1°, θmin = 2.1°
φ scans	h = −20→21
24106 measured reflections	k = −15→15
6128 independent reflections	l = −17→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.082	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0429P)^2 + 1.705P] where P = (Fo^2 + 2Fc^2)/3
6128 reflections	(Δ/σ)max = 0.002
490 parameters	Δρmax = 0.39 e Å^−3
12 restraints	Δρmin = −0.36 e Å^−3

Special details

Experimental. The data were collected on a Stoe Imaging Plate Diffraction System (IPDS) equipped with an Oxford Cryosystems cooler device. The crystal-to-detector distance was 70 mm. 133 frames (5 min per frame) were obtained with 0 < φ < 199.5° and with the crystals oscillatated through 1.5° in φ. Crystal decay was monitored by measuring 200 reflections per frame.

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.

L·S·Q. Planes for BP41

Crystal data a = 17.0766(0.0016) alpha= 90.00(0.00) b = 12.7466(0.0010) beta = 93.22(0.01) c = 14.4217(0.0014) gamma= 90.00(0.00) V = 3134.20 (0.49) cubic-Angstrom

Weighted least-squares planes through the starred atoms (Nardelli, Musatti, Domiano & Andreetti Ric·Sci.(1965),15(II—A),807). Equation of the plane: m1*X+m2*Y+m3*Z=d

Plane 1 basal plane m1 = -0.11863(0.00054) m2 = -0.98980(0.00006) m3 = -0.07895(0.00055) D = -2.87346(0.00667) Atom d s d/s (d/s)**2 N1 * 0.1927 0.0017 116.473 13565.894 N11 * -0.1921 0.0017 - 116.017 13459.836 N21 * -0.2344 0.0017 - 141.560 20039.318 N30 * 0.1994 0.0015 130.329 16985.543 Zn1 - 0.0491 0.0003 - 191.346 36613.418 ============ Sum((d/s)**2) for starred atoms 64050.590 Chi-squared at 95% for 1 degrees of freedom: 3.84 The group of atoms deviates significantly from planarity

Plane 2 P1 m1 = -0.99061(0.00002) m2 = 0.12042(0.00054) m3 = -0.06476(0.00061) D = -12.15017(0.00214) Atom d s d/s (d/s)**2 N1 * 0.0061 0.0016 3.910 15.288 C2 * -0.0344 0.0017 - 19.933 397.328 C1 * 0.0590 0.0017 34.229 1171.626 O1 * -0.0310 0.0014 - 22.430 503.089 Zn1 * 0.0003 0.0003 1.363 1.857 O2 0.2329 0.0015 150.537 22661.490 ============ Sum((d/s)**2) for starred atoms 2089.188 Chi-squared at 95% for 2 degrees of freedom: 5.99 The group of atoms deviates significantly from planarity

Plane 3 P2 m1 = -0.03446(0.00050) m2 = 0.17328(0.00058) m3 = -0.98427(0.00010) D = -2.35330(0.00570) Atom d s d/s (d/s)**2 N11 * 0.0673 0.0016 42.393 1797.186 C12 * -0.0552 0.0017 - 31.780 1009.963 C11 * -0.0388 0.0019 - 20.654 426.608 O11 * 0.0401 0.0013 30.876 953.347 Zn1 * -0.0006 0.0002 - 3.521 12.395 O12 - 0.0865 0.0019 - 46.406 2153.531 ============ Sum((d/s)**2) for starred atoms 4199.499 Chi-squared at 95% for 2 degrees of freedom: 5.99 The group of atoms deviates significantly from planarity

Plane 4 P3 m1 = -0.99728(0.00000) m2 = 0.06749(0.00054) m3 = -0.02967(0.00048) D = -12.11823(0.00303) Atom d s d/s (d/s)**2 N1 * -0.0041 0.0016 - 2.646 7.000 C2 * 0.0355 0.0017 20.597 424.226 C3 * 0.0101 0.0017 5.870 34.458 C4 * -0.0339 0.0021 - 16.441 270.307 C5 * -0.0312 0.0022 - 14.006 196.181 C6 * 0.0172 0.0022 7.712 59.477 C7 * 0.0200 0.0022 8.984 80.720 C8 * 0.0130 0.0019 6.850 46.922 C9 * -0.0092 0.0022 - 4.137 17.115 C10 * -0.0367 0.0021 - 17.838 318.184 Zn1 - 0.1057 0.0003 - 421.622 177764.734 ============ Sum((d/s)**2) for starred atoms 1454.591 Chi-squared at 95% for 7 degrees of freedom: 14.10 The group of atoms deviates significantly from planarity

Plane 5 P4 m1 = 0.04959(0.00051) m2 = 0.27842(0.00060) m3 = -0.95918(0.00016) D = -0.87042(0.00785) Atom d s d/s (d/s)**2 N11 * -0.0271 0.0016 - 17.049 290.658 C12 * 0.0286 0.0017 16.380 268.305 C13 * 0.0291 0.0019 15.434 238.213 C14 * -0.0111 0.0023 - 4.799 23.032 C15 * -0.0437 0.0027 - 15.961 254.747 C16 * -0.0363 0.0029 - 12.593 158.577 C17 * 0.0097 0.0027 3.540 12.532 C18 * 0.0330 0.0022 15.218 231.596 C19 * 0.0225 0.0023 9.778 95.616 C20 * -0.0294 0.0020 - 14.485 209.813 Zn1 - 0.2590 0.0002 - 1507.281 2271895.250 ============ Sum((d/s)**2) for starred atoms 1783.090 Chi-squared at 95% for 7 degrees of freedom: 14.10 The group of atoms deviates significantly from planarity

Plane 6 P5 m1 = 0.12096(0.00033) m2 = 0.98437(0.00002) m3 = -0.12800(0.00033) D = 2.71189(0.00336) Atom d s d/s (d/s)**2 N21 * 0.0038 0.0017 2.304 5.308 C22 * 0.0319 0.0023 13.966 195.038 C23 * 0.0275 0.0023 11.991 143.783 C24 * -0.0172 0.0022 - 7.937 62.994 C25 * -0.0120 0.0022 - 5.528 30.554 C26 * 0.0121 0.0022 5.594 31.293 C27 * 0.0172 0.0020 8.433 71.118 C28 * 0.0202 0.0022 9.335 87.150 C29 * 0.0022 0.0020 1.101 1.211 N30 * -0.0226 0.0015 - 14.759 217.841 C31 * -0.0126 0.0018 - 7.080 50.127 C32 * 0.0077 0.0019 4.032 16.257 C33 * -0.0157 0.0020 - 7.710 59.437 C34 * -0.0089 0.0018 - 4.987 24.867 Zn1 - 0.2213 0.0003 - 865.536 749152.625 ============ Sum((d/s)**2) for starred atoms 996.979 Chi-squared at 95% for 11 degrees of freedom: 19.70 The group of atoms deviates significantly from planarity

Dihedral angles formed by LSQ-planes Plane - plane angle (s.u.) angle (s.u.) 1 2 89.80 (0.04) 90.20 (0.04) 1 3 84.85 (0.04) 95.15 (0.04) 1 4 86.91 (0.04) 93.09 (0.04) 1 5 78.13 (0.04) 101.87 (0.04) 1 6 11.88 (0.04) 168.12 (0.04) 2 3 83.18 (0.05) 96.82 (0.05) 2 4 3.66 (0.04) 176.34 (0.04) 2 5 87.33 (0.05) 92.67 (0.05) 2 6 89.60 (0.04) 90.40 (0.04) 3 4 85.68 (0.04) 94.32 (0.04) 3 5 7.85 (0.05) 172.15 (0.05) 3 6 73.00 (0.04) 107.00 (0.04) 4 5 89.87 (0.04) 90.13 (0.04) 4 6 87.11 (0.04) 92.89 (0.04) 5 6 66.24 (0.04) 113.76 (0.04)

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Zn1	0.726360 (12)	0.102463 (17)	0.152204 (14)	0.02141 (8)
O1	0.71342 (8)	−0.05996 (11)	0.15910 (9)	0.0254 (3)
N1	0.72212 (9)	0.07189 (13)	0.29871 (10)	0.0221 (3)
C1	0.70372 (10)	−0.10158 (15)	0.23760 (13)	0.0227 (4)
O2	0.68499 (9)	−0.19362 (11)	0.25019 (10)	0.0355 (3)
C2	0.71527 (10)	−0.02798 (15)	0.32191 (13)	0.0209 (4)
C3	0.71721 (10)	−0.06084 (15)	0.41643 (13)	0.0226 (4)
C4	0.71512 (12)	−0.16656 (17)	0.44631 (14)	0.0294 (4)
H4	0.7133	−0.2202	0.4026	0.035*
C5	0.71581 (13)	−0.19070 (18)	0.53873 (15)	0.0357 (5)
H5	0.7145	−0.2606	0.5570	0.043*
C6	0.71849 (13)	−0.11123 (19)	0.60639 (15)	0.0373 (5)
H6	0.7172	−0.1287	0.6689	0.045*
C7	0.72293 (13)	−0.00867 (19)	0.58067 (14)	0.0351 (5)
H7	0.7262	0.0435	0.6258	0.042*
C8	0.72262 (11)	0.01901 (16)	0.48554 (13)	0.0267 (4)
C9	0.72861 (13)	0.12423 (17)	0.45744 (14)	0.0307 (4)
H9	0.7321	0.1777	0.5014	0.037*
C10	0.72932 (12)	0.14694 (16)	0.36552 (13)	0.0285 (4)
H10	0.7349	0.2165	0.3476	0.034*
O11	0.75991 (7)	0.25589 (10)	0.17189 (9)	0.0244 (3)
N11	0.84999 (9)	0.09486 (13)	0.14107 (11)	0.0232 (3)
C11	0.83298 (11)	0.27654 (16)	0.17765 (13)	0.0257 (4)
O12	0.86124 (9)	0.36379 (12)	0.19347 (13)	0.0431 (4)
C12	0.88741 (11)	0.18316 (15)	0.16196 (12)	0.0229 (4)
C13	0.97125 (11)	0.18813 (16)	0.16832 (13)	0.0274 (4)
C14	1.01524 (12)	0.27761 (19)	0.19684 (16)	0.0361 (5)
H14	0.9896	0.3393	0.2114	0.043*
C15	1.09539 (13)	0.2737 (2)	0.20309 (19)	0.0462 (6)
H15	1.1237	0.3330	0.2220	0.055*
C16	1.13577 (13)	0.1818 (2)	0.1815 (2)	0.0497 (6)
H16	1.1903	0.1805	0.1864	0.060*
C17	1.09527 (13)	0.0946 (2)	0.15334 (19)	0.0451 (6)
H17	1.1223	0.0342	0.1383	0.054*
C18	1.01235 (12)	0.09497 (18)	0.14668 (15)	0.0322 (5)
C19	0.96952 (13)	0.00399 (18)	0.12151 (16)	0.0353 (5)
H19	0.9954	−0.0570	0.1054	0.042*
C20	0.89018 (12)	0.00630 (17)	0.12100 (14)	0.0301 (4)
H20	0.8623	−0.0547	0.1064	0.036*
N21	0.60127 (9)	0.13854 (13)	0.13632 (11)	0.0236 (3)
C22	0.55284 (12)	0.15906 (18)	0.20294 (14)	0.0312 (4)
H22	0.5740	0.1668	0.2634	0.037*
C23	0.47204 (12)	0.16952 (18)	0.18687 (16)	0.0345 (5)
H23	0.4402	0.1844	0.2354	0.041*
C24	0.44048 (11)	0.15745 (17)	0.09826 (15)	0.0316 (4)
H24	0.3865	0.1620	0.0863	0.038*
C25	0.46146 (12)	0.12839 (17)	−0.06995 (15)	0.0311 (4)
H25	0.4080	0.1337	−0.0853	0.037*
C26	0.51149 (12)	0.11164 (17)	−0.13739 (14)	0.0315 (4)
H26	0.4920	0.1069	−0.1988	0.038*
C27	0.64850 (13)	0.08230 (16)	−0.18388 (13)	0.0303 (4)
H27	0.6315	0.0758	−0.2460	0.036*
C28	0.72666 (12)	0.07363 (17)	−0.15829 (14)	0.0295 (4)
H28	0.7633	0.0618	−0.2025	0.035*
C29	0.75047 (11)	0.08291 (16)	−0.06371 (13)	0.0256 (4)
H29	0.8036	0.0773	−0.0465	0.031*
N30	0.70059 (9)	0.09930 (12)	0.00194 (10)	0.0215 (3)
C31	0.62336 (11)	0.10884 (14)	−0.02369 (12)	0.0212 (4)
C32	0.59398 (12)	0.10095 (15)	−0.11645 (13)	0.0256 (4)
C33	0.48970 (11)	0.13819 (16)	0.02538 (14)	0.0261 (4)
C34	0.57026 (11)	0.12901 (14)	0.04827 (13)	0.0216 (4)
O50	0.92230 (12)	0.28564 (19)	0.43903 (15)	0.0648 (6)
C50A	0.9353 (2)	0.1992 (3)	0.4157 (2)	0.0477 (8)	0.73
H50A	0.8921	0.1626	0.3904	0.057*	0.73
N50	1.00252 (13)	0.1457 (2)	0.41978 (15)	0.0497 (5)
C51A	1.0152 (4)	0.0482 (4)	0.3812 (3)	0.0750 (14)	0.73
H511	0.9659	0.0185	0.3594	0.112*	0.73
H512	1.0399	0.0030	0.4273	0.112*	0.73
H513	1.0485	0.0556	0.3302	0.112*	0.73
C52A	1.0737 (2)	0.2076 (4)	0.4535 (3)	0.0592 (10)	0.73
H521	1.0575	0.2685	0.4865	0.089*	0.73
H522	1.1024	0.2290	0.4013	0.089*	0.73
H523	1.1066	0.1647	0.4941	0.089*	0.73
C50B	0.9847 (6)	0.2334 (9)	0.4409 (7)	0.057 (3)	0.27
H50B	1.0276	0.2719	0.4645	0.068*	0.27
C51B	0.9353 (6)	0.0646 (9)	0.3891 (8)	0.056 (3)	0.27
H514	0.8860	0.1008	0.3818	0.084*	0.27
H515	0.9321	0.0114	0.4358	0.084*	0.27
H516	0.9471	0.0327	0.3313	0.084*	0.27
C52B	1.0759 (6)	0.0826 (10)	0.4285 (8)	0.060 (3)	0.27
H524	1.0656	0.0171	0.4582	0.091*	0.27
H525	1.1152	0.1206	0.4650	0.091*	0.27
H526	1.0943	0.0696	0.3678	0.091*	0.27
N40	0.5000	0.0000	0.5000	0.0426 (7)
O40	0.5031 (4)	−0.0095 (5)	0.3471 (3)	0.0893 (17)	0.50
C40	0.5000 (4)	0.0612 (5)	0.4135 (4)	0.0610 (15)	0.50
H40	0.4983	0.1338	0.4071	0.073*	0.50
C41	0.4888 (4)	−0.1052 (4)	0.4980 (5)	0.0650 (17)	0.50
H411	0.5386	−0.1401	0.5033	0.097*	0.50
H412	0.4616	−0.1245	0.4404	0.097*	0.50
H413	0.4581	−0.1255	0.5488	0.097*	0.50
C42	0.5023 (4)	−0.0587 (5)	0.4180 (4)	0.0571 (14)	0.50
H421	0.5392	−0.0277	0.3784	0.086*	0.50
H422	0.4511	−0.0592	0.3867	0.086*	0.50
H423	0.5179	−0.1293	0.4329	0.086*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.02219 (12)	0.02467 (13)	0.01718 (11)	0.00007 (8)	−0.00051 (7)	0.00068 (8)
O1	0.0310 (7)	0.0256 (7)	0.0193 (6)	−0.0030 (5)	−0.0002 (5)	−0.0030 (5)
N1	0.0274 (8)	0.0209 (8)	0.0179 (7)	−0.0009 (6)	−0.0011 (6)	−0.0001 (6)
C1	0.0206 (8)	0.0231 (9)	0.0242 (9)	−0.0005 (7)	−0.0004 (7)	−0.0024 (8)
O2	0.0531 (9)	0.0233 (8)	0.0301 (8)	−0.0099 (6)	0.0023 (6)	−0.0044 (6)
C2	0.0187 (8)	0.0224 (9)	0.0214 (9)	−0.0020 (7)	−0.0008 (7)	0.0005 (7)
C3	0.0210 (8)	0.0251 (10)	0.0217 (9)	−0.0037 (7)	−0.0006 (7)	0.0002 (8)
C4	0.0337 (10)	0.0265 (11)	0.0277 (10)	−0.0062 (8)	−0.0007 (8)	0.0027 (8)
C5	0.0389 (11)	0.0326 (12)	0.0350 (11)	−0.0093 (9)	−0.0023 (9)	0.0118 (9)
C6	0.0437 (12)	0.0452 (14)	0.0226 (10)	−0.0126 (10)	−0.0025 (9)	0.0107 (9)
C7	0.0458 (12)	0.0399 (13)	0.0193 (9)	−0.0110 (10)	−0.0006 (8)	−0.0003 (9)
C8	0.0299 (10)	0.0299 (11)	0.0202 (9)	−0.0050 (8)	−0.0007 (7)	0.0009 (8)
C9	0.0435 (12)	0.0267 (11)	0.0216 (9)	−0.0039 (8)	−0.0007 (8)	−0.0050 (8)
C10	0.0417 (11)	0.0212 (10)	0.0223 (9)	−0.0026 (8)	−0.0001 (8)	−0.0012 (8)
O11	0.0242 (6)	0.0235 (7)	0.0258 (7)	0.0018 (5)	0.0030 (5)	0.0023 (5)
N11	0.0236 (8)	0.0250 (8)	0.0207 (7)	0.0010 (6)	0.0001 (6)	0.0009 (6)
C11	0.0273 (9)	0.0251 (10)	0.0250 (9)	0.0006 (8)	0.0035 (7)	0.0023 (8)
O12	0.0324 (8)	0.0251 (8)	0.0721 (12)	−0.0024 (6)	0.0065 (8)	−0.0069 (8)
C12	0.0246 (9)	0.0255 (10)	0.0185 (8)	0.0007 (7)	0.0005 (7)	0.0023 (7)
C13	0.0259 (9)	0.0320 (11)	0.0243 (9)	0.0002 (8)	0.0011 (7)	0.0049 (8)
C14	0.0293 (10)	0.0379 (13)	0.0408 (12)	−0.0044 (9)	0.0002 (9)	−0.0004 (10)
C15	0.0306 (11)	0.0507 (15)	0.0568 (15)	−0.0111 (10)	−0.0013 (10)	0.0024 (12)
C16	0.0225 (10)	0.0648 (18)	0.0614 (16)	−0.0010 (11)	0.0006 (10)	0.0096 (14)
C17	0.0292 (11)	0.0510 (15)	0.0557 (15)	0.0100 (10)	0.0058 (10)	0.0065 (12)
C18	0.0266 (10)	0.0376 (12)	0.0327 (11)	0.0046 (9)	0.0041 (8)	0.0041 (9)
C19	0.0343 (11)	0.0313 (12)	0.0405 (12)	0.0104 (9)	0.0044 (9)	−0.0019 (9)
C20	0.0327 (11)	0.0249 (10)	0.0329 (11)	0.0042 (8)	0.0022 (8)	−0.0021 (8)
N21	0.0226 (8)	0.0270 (8)	0.0213 (8)	0.0009 (6)	0.0009 (6)	0.0000 (7)
C22	0.0298 (10)	0.0390 (12)	0.0251 (10)	0.0033 (8)	0.0047 (8)	−0.0018 (9)
C23	0.0308 (10)	0.0379 (12)	0.0359 (11)	0.0061 (9)	0.0114 (9)	0.0006 (9)
C24	0.0225 (9)	0.0297 (11)	0.0427 (12)	0.0054 (8)	0.0024 (8)	0.0044 (9)
C25	0.0255 (10)	0.0302 (11)	0.0363 (11)	0.0011 (8)	−0.0087 (8)	0.0022 (9)
C26	0.0337 (11)	0.0320 (11)	0.0274 (10)	−0.0005 (8)	−0.0104 (8)	0.0010 (9)
C27	0.0427 (11)	0.0299 (11)	0.0180 (9)	0.0011 (9)	−0.0023 (8)	0.0004 (8)
C28	0.0380 (11)	0.0310 (11)	0.0199 (9)	0.0034 (8)	0.0051 (8)	0.0007 (8)
C29	0.0262 (9)	0.0292 (11)	0.0215 (9)	0.0026 (7)	0.0026 (7)	0.0005 (8)
N30	0.0235 (7)	0.0234 (8)	0.0174 (7)	0.0007 (6)	−0.0004 (6)	0.0010 (6)
C31	0.0246 (9)	0.0181 (9)	0.0205 (9)	−0.0004 (7)	−0.0013 (7)	0.0011 (7)
C32	0.0328 (10)	0.0215 (9)	0.0220 (9)	−0.0006 (8)	−0.0039 (7)	0.0027 (7)
C33	0.0239 (9)	0.0213 (9)	0.0328 (10)	0.0015 (7)	−0.0015 (8)	0.0029 (8)
C34	0.0235 (9)	0.0181 (9)	0.0230 (9)	−0.0005 (7)	−0.0010 (7)	0.0019 (7)
O50	0.0593 (13)	0.0687 (15)	0.0670 (13)	0.0165 (11)	0.0081 (10)	0.0065 (11)
C50A	0.044 (2)	0.058 (2)	0.0415 (19)	−0.0055 (18)	0.0044 (15)	−0.0001 (17)
N50	0.0496 (13)	0.0626 (16)	0.0370 (11)	0.0101 (11)	0.0028 (9)	−0.0025 (11)
C51A	0.124 (4)	0.052 (3)	0.051 (2)	0.017 (3)	0.020 (3)	−0.003 (2)
C52A	0.043 (2)	0.084 (3)	0.050 (2)	−0.0006 (19)	−0.0011 (16)	0.004 (2)
C50B	0.057 (7)	0.072 (8)	0.041 (5)	−0.006 (6)	−0.004 (5)	0.001 (5)
C51B	0.060 (6)	0.054 (6)	0.053 (6)	−0.014 (5)	0.000 (5)	0.016 (5)
C52B	0.050 (6)	0.078 (9)	0.053 (6)	0.015 (6)	0.001 (5)	0.010 (6)
N40	0.0580 (18)	0.0398 (16)	0.0299 (14)	−0.0058 (13)	0.0030 (12)	−0.0022 (12)
O40	0.140 (5)	0.099 (4)	0.028 (2)	−0.018 (3)	−0.002 (2)	0.005 (2)
C40	0.083 (4)	0.055 (4)	0.045 (3)	0.006 (3)	0.000 (3)	0.009 (3)
C41	0.081 (4)	0.033 (3)	0.082 (5)	0.003 (3)	0.015 (3)	−0.005 (3)
C42	0.073 (4)	0.046 (3)	0.051 (3)	0.004 (3)	−0.002 (3)	−0.008 (3)

Geometric parameters (Å, º)

Zn1—O11	2.0531 (14)	C24—H24	0.9300
Zn1—O1	2.0851 (14)	C25—C26	1.347 (3)
Zn1—N11	2.1285 (16)	C25—C33	1.437 (3)
Zn1—N1	2.1537 (15)	C25—H25	0.9300
Zn1—N21	2.1845 (15)	C26—C32	1.430 (3)
Zn1—N30	2.1873 (15)	C26—H26	0.9300
O1—C1	1.270 (2)	C27—C28	1.369 (3)
N1—C2	1.323 (2)	C27—C32	1.404 (3)
N1—C10	1.358 (3)	C27—H27	0.9300
C1—O2	1.232 (2)	C28—C29	1.406 (3)
C1—C2	1.540 (3)	C28—H28	0.9300
C2—C3	1.425 (3)	C29—N30	1.325 (2)
C3—C4	1.416 (3)	C29—H29	0.9300
C3—C8	1.424 (3)	N30—C31	1.355 (2)
C4—C5	1.367 (3)	C31—C32	1.406 (3)
C4—H4	0.9300	C31—C34	1.439 (3)
C5—C6	1.406 (3)	C33—C34	1.402 (3)
C5—H5	0.9300	O50—C50A	1.177 (4)
C6—C7	1.362 (3)	O50—C50B	1.256 (10)
C6—H6	0.9300	C50A—N50	1.333 (4)
C7—C8	1.416 (3)	C50A—H50A	0.9300
C7—H7	0.9300	N50—C50B	1.202 (10)
C8—C9	1.406 (3)	N50—C51A	1.383 (5)
C9—C10	1.358 (3)	N50—C52B	1.489 (9)
C9—H9	0.9300	N50—C52A	1.507 (4)
C10—H10	0.9300	N50—C51B	1.589 (9)
O11—C11	1.273 (2)	C51A—H511	0.9600
N11—C12	1.321 (3)	C51A—H512	0.9600
N11—C20	1.361 (3)	C51A—H513	0.9600
C11—O12	1.229 (3)	C52A—H521	0.9600
C11—C12	1.535 (3)	C52A—H522	0.9600
C12—C13	1.431 (3)	C52A—H523	0.9600
C13—C14	1.414 (3)	C50B—H50B	0.9300
C13—C18	1.423 (3)	C51B—H514	0.9600
C14—C15	1.368 (3)	C51B—H515	0.9600
C14—H14	0.9300	C51B—H516	0.9600
C15—C16	1.403 (4)	C52B—H524	0.9600
C15—H15	0.9300	C52B—H525	0.9600
C16—C17	1.359 (4)	C52B—H526	0.9600
C16—H16	0.9300	N40—C41	1.355 (6)
C17—C18	1.414 (3)	N40—C41^i	1.355 (6)
C17—H17	0.9300	N40—C42^i	1.401 (6)
C18—C19	1.408 (3)	N40—C42	1.401 (6)
C19—C20	1.355 (3)	N40—C40	1.472 (6)
C19—H19	0.9300	N40—C40^i	1.472 (6)
C20—H20	0.9300	O40—C40	1.318 (8)
N21—C22	1.328 (2)	C40—H40	0.9300
N21—C34	1.354 (2)	C41—H411	0.9600
C22—C23	1.393 (3)	C41—H412	0.9600
C22—H22	0.9300	C41—H413	0.9600
C23—C24	1.367 (3)	C42—H421	0.9600
C23—H23	0.9300	C42—H422	0.9600
C24—C33	1.404 (3)	C42—H423	0.9600
O11—Zn1—O1	165.63 (5)	C33—C24—H24	120.1
O11—Zn1—N11	77.50 (6)	C26—C25—C33	120.82 (18)
O1—Zn1—N11	93.82 (6)	C26—C25—H25	119.6
O11—Zn1—N1	93.51 (6)	C33—C25—H25	119.6
O1—Zn1—N1	76.35 (6)	C25—C26—C32	121.31 (18)
N11—Zn1—N1	98.85 (6)	C25—C26—H26	119.3
O11—Zn1—N21	94.45 (6)	C32—C26—H26	119.3
O1—Zn1—N21	96.23 (6)	C28—C27—C32	120.10 (18)
N11—Zn1—N21	165.91 (6)	C28—C27—H27	120.0
N1—Zn1—N21	93.12 (6)	C32—C27—H27	120.0
O11—Zn1—N30	101.16 (6)	C27—C28—C29	118.61 (18)
O1—Zn1—N30	90.74 (5)	C27—C28—H28	120.7
N11—Zn1—N30	94.00 (6)	C29—C28—H28	120.7
N1—Zn1—N30	162.29 (6)	N30—C29—C28	122.95 (18)
N21—Zn1—N30	76.04 (6)	N30—C29—H29	118.5
N1—C2—C1	113.32 (15)	C28—C29—H29	118.5
C1—O1—Zn1	118.48 (12)	C29—N30—C31	118.29 (16)
C2—N1—C10	120.26 (16)	C29—N30—Zn1	127.53 (13)
C2—N1—Zn1	115.50 (12)	C31—N30—Zn1	114.03 (12)
O2—C1—O1	125.25 (18)	N30—C31—C32	122.90 (17)
O2—C1—C2	119.13 (17)	N30—C31—C34	117.54 (16)
O1—C1—C2	115.61 (16)	C32—C31—C34	119.56 (17)
C10—N1—Zn1	124.17 (13)	C27—C32—C31	117.14 (18)
N1—C2—C3	121.82 (17)	C27—C32—C26	123.61 (18)
C3—C2—C1	124.85 (17)	C31—C32—C26	119.25 (18)
C4—C3—C8	117.98 (17)	C34—C33—C24	117.34 (18)
C4—C3—C2	124.85 (18)	C34—C33—C25	119.37 (18)
C8—C3—C2	117.17 (17)	C24—C33—C25	123.28 (18)
C5—C4—C3	120.8 (2)	N21—C34—C33	122.73 (17)
C5—C4—H4	119.6	C33—C34—C31	119.66 (17)
C3—C4—H4	119.6	O50—C50A—N50	130.0 (4)
C4—C5—C6	120.8 (2)	O50—C50A—H50A	115.0
C4—C5—H5	119.6	N50—C50A—H50A	115.0
C6—C5—H5	119.6	C50B—N50—C51A	169.9 (6)
C7—C6—C5	120.18 (19)	C50A—N50—C51A	126.5 (4)
C7—C6—H6	119.9	C50B—N50—C52B	134.8 (8)
C5—C6—H6	119.9	C50A—N50—C52B	177.0 (5)
C6—C7—C8	120.4 (2)	C51A—N50—C52B	53.1 (5)
C6—C7—H7	119.8	C50B—N50—C52A	69.1 (6)
C8—C7—H7	119.8	C50A—N50—C52A	115.0 (3)
C9—C8—C7	121.36 (19)	C51A—N50—C52A	117.3 (3)
C9—C8—C3	118.87 (17)	C52B—N50—C52A	66.1 (6)
C7—C8—C3	119.77 (19)	C50B—N50—C51B	119.1 (7)
C10—C9—C8	119.31 (19)	C50A—N50—C51B	73.4 (5)
C10—C9—H9	120.3	C51A—N50—C51B	55.3 (5)
C8—C9—H9	120.3	C52B—N50—C51B	105.3 (7)
C9—C10—N1	122.48 (19)	C52A—N50—C51B	171.0 (5)
C9—C10—H10	118.8	N50—C51A—H511	109.5
N1—C10—H10	118.8	N50—C51A—H512	109.5
C11—O11—Zn1	118.08 (12)	N50—C51A—H513	109.5
N11—C12—C11	113.91 (16)	N50—C52A—H521	109.5
O11—C11—C12	115.43 (17)	N50—C52A—H522	109.5
C12—N11—C20	120.81 (17)	N50—C52A—H523	109.5
C12—N11—Zn1	114.41 (12)	N50—C50B—O50	135.6 (10)
C20—N11—Zn1	124.62 (13)	N50—C50B—H50B	112.2
O12—C11—O11	124.92 (18)	O50—C50B—H50B	112.2
O12—C11—C12	119.64 (17)	N50—C51B—H514	109.5
N11—C12—C13	121.46 (17)	N50—C51B—H515	109.5
C13—C12—C11	124.63 (17)	H514—C51B—H515	109.5
C14—C13—C18	118.45 (19)	N50—C51B—H516	109.5
C14—C13—C12	124.58 (19)	H514—C51B—H516	109.5
C18—C13—C12	116.94 (18)	H515—C51B—H516	109.5
C15—C14—C13	120.2 (2)	N50—C52B—H524	109.5
C15—C14—H14	119.9	N50—C52B—H525	109.5
C13—C14—H14	119.9	H524—C52B—H525	109.5
C14—C15—C16	121.2 (2)	N50—C52B—H526	109.5
C14—C15—H15	119.4	H524—C52B—H526	109.5
C16—C15—H15	119.4	H525—C52B—H526	109.5
C17—C16—C15	120.1 (2)	C41—N40—C41^i	180.000 (1)
C17—C16—H16	120.0	C41—N40—C42^i	122.4 (4)
C15—C16—H16	120.0	C41^i—N40—C42^i	57.6 (4)
C16—C17—C18	120.6 (2)	C41—N40—C42	57.6 (4)
C16—C17—H17	119.7	C41^i—N40—C42	122.4 (4)
C18—C17—H17	119.7	C42^i—N40—C42	180.000 (1)
C19—C18—C17	121.2 (2)	C41—N40—C40	120.9 (4)
C19—C18—C13	119.24 (19)	C41^i—N40—C40	59.1 (4)
C17—C18—C13	119.5 (2)	C42^i—N40—C40	115.7 (4)
C20—C19—C18	119.2 (2)	C42—N40—C40	64.3 (4)
C20—C19—H19	120.4	C41—N40—C40^i	59.1 (4)
C18—C19—H19	120.4	C41^i—N40—C40^i	120.9 (4)
C19—C20—N11	122.2 (2)	C42^i—N40—C40^i	64.3 (4)
C19—C20—H20	118.9	C42—N40—C40^i	115.7 (4)
N11—C20—H20	118.9	C40—N40—C40^i	180.000 (1)
C22—N21—C34	118.00 (16)	O40—C40—N40	104.8 (5)
N21—C34—C31	117.61 (16)	O40—C40—H40	127.6
C22—N21—Zn1	127.62 (13)	N40—C40—H40	127.6
C34—N21—Zn1	114.09 (12)	N40—C41—H411	109.5
N21—C22—C23	123.35 (19)	N40—C41—H412	109.5
N21—C22—H22	118.3	N40—C41—H413	109.5
C23—C22—H22	118.3	N40—C42—H421	109.5
C24—C23—C22	118.66 (19)	N40—C42—H422	109.5
C24—C23—H23	120.7	H421—C42—H422	109.5
C22—C23—H23	120.7	N40—C42—H423	109.5
C23—C24—C33	119.88 (18)	H421—C42—H423	109.5
C23—C24—H24	120.1	H422—C42—H423	109.5
O11—Zn1—O1—C1	50.8 (3)	C14—C13—C18—C19	177.7 (2)
N11—Zn1—O1—C1	102.92 (13)	C12—C13—C18—C19	−0.6 (3)
N1—Zn1—O1—C1	4.73 (13)	C14—C13—C18—C17	−0.6 (3)
N21—Zn1—O1—C1	−86.98 (13)	C12—C13—C18—C17	−178.9 (2)
N30—Zn1—O1—C1	−163.02 (13)	C17—C18—C19—C20	176.4 (2)
O11—Zn1—N1—C2	−168.59 (13)	C13—C18—C19—C20	−1.9 (3)
O1—Zn1—N1—C2	1.09 (12)	C18—C19—C20—N11	2.2 (3)
N11—Zn1—N1—C2	−90.71 (13)	C12—N11—C20—C19	0.1 (3)
N21—Zn1—N1—C2	96.75 (13)	Zn1—N11—C20—C19	−174.98 (16)
N30—Zn1—N1—C2	45.3 (3)	O11—Zn1—N21—C22	−78.71 (18)
O11—Zn1—N1—C10	8.50 (16)	O1—Zn1—N21—C22	91.66 (18)
O1—Zn1—N1—C10	178.19 (16)	N11—Zn1—N21—C22	−133.1 (3)
N11—Zn1—N1—C10	86.38 (16)	N1—Zn1—N21—C22	15.06 (18)
N21—Zn1—N1—C10	−86.16 (16)	N30—Zn1—N21—C22	−179.12 (19)
N30—Zn1—N1—C10	−137.6 (2)	O11—Zn1—N21—C34	107.59 (13)
Zn1—O1—C1—O2	169.73 (15)	O1—Zn1—N21—C34	−82.04 (13)
Zn1—O1—C1—C2	−9.0 (2)	N11—Zn1—N21—C34	53.2 (3)
C10—N1—C2—C3	−1.7 (3)	N1—Zn1—N21—C34	−158.64 (13)
Zn1—N1—C2—C3	175.55 (13)	N30—Zn1—N21—C34	7.17 (13)
C10—N1—C2—C1	177.23 (16)	C34—N21—C22—C23	1.0 (3)
Zn1—N1—C2—C1	−5.56 (19)	Zn1—N21—C22—C23	−172.44 (16)
O2—C1—C2—N1	−169.22 (17)	N21—C22—C23—C24	0.5 (3)
O1—C1—C2—N1	9.6 (2)	C22—C23—C24—C33	−2.0 (3)
O2—C1—C2—C3	9.6 (3)	C33—C25—C26—C32	1.3 (3)
O1—C1—C2—C3	−171.54 (17)	C32—C27—C28—C29	0.5 (3)
N1—C2—C3—C4	−175.89 (17)	C27—C28—C29—N30	0.3 (3)
C1—C2—C3—C4	5.3 (3)	C28—C29—N30—C31	−0.9 (3)
N1—C2—C3—C8	3.3 (3)	C28—C29—N30—Zn1	174.42 (15)
C1—C2—C3—C8	−175.46 (16)	O11—Zn1—N30—C29	85.98 (17)
C8—C3—C4—C5	2.0 (3)	O1—Zn1—N30—C29	−85.93 (17)
C2—C3—C4—C5	−178.80 (19)	N11—Zn1—N30—C29	7.95 (17)
C3—C4—C5—C6	0.1 (3)	N1—Zn1—N30—C29	−128.6 (2)
C4—C5—C6—C7	−2.1 (3)	N21—Zn1—N30—C29	177.84 (17)
C5—C6—C7—C8	1.8 (3)	O11—Zn1—N30—C31	−98.55 (13)
C6—C7—C8—C9	−178.8 (2)	O1—Zn1—N30—C31	89.54 (13)
C6—C7—C8—C3	0.3 (3)	N11—Zn1—N30—C31	−176.58 (13)
C4—C3—C8—C9	176.95 (18)	N1—Zn1—N30—C31	46.9 (3)
C2—C3—C8—C9	−2.3 (3)	N21—Zn1—N30—C31	−6.69 (12)
C4—C3—C8—C7	−2.2 (3)	C29—N30—C31—C32	0.7 (3)
C2—C3—C8—C7	178.52 (18)	Zn1—N30—C31—C32	−175.20 (14)
C7—C8—C9—C10	179.0 (2)	C29—N30—C31—C34	−178.60 (17)
C3—C8—C9—C10	−0.2 (3)	Zn1—N30—C31—C34	5.5 (2)
C8—C9—C10—N1	2.0 (3)	C28—C27—C32—C31	−0.7 (3)
C2—N1—C10—C9	−1.1 (3)	C28—C27—C32—C26	179.6 (2)
Zn1—N1—C10—C9	−178.04 (16)	N30—C31—C32—C27	0.0 (3)
O1—Zn1—O11—C11	47.5 (3)	C34—C31—C32—C27	179.35 (17)
N11—Zn1—O11—C11	−6.26 (13)	N30—C31—C32—C26	179.77 (18)
N1—Zn1—O11—C11	92.04 (14)	C34—C31—C32—C26	−0.9 (3)
N21—Zn1—O11—C11	−174.55 (13)	C25—C26—C32—C27	179.3 (2)
N30—Zn1—O11—C11	−97.92 (14)	C25—C26—C32—C31	−0.4 (3)
O11—Zn1—N11—C12	7.44 (12)	C23—C24—C33—C34	1.9 (3)
O1—Zn1—N11—C12	−160.99 (13)	C23—C24—C33—C25	−177.7 (2)
N1—Zn1—N11—C12	−84.22 (13)	C26—C25—C33—C34	−0.7 (3)
N21—Zn1—N11—C12	63.6 (3)	C26—C25—C33—C24	178.9 (2)
N30—Zn1—N11—C12	108.00 (13)	C22—N21—C34—C33	−1.1 (3)
O11—Zn1—N11—C20	−177.20 (16)	Zn1—N21—C34—C33	173.29 (14)
O1—Zn1—N11—C20	14.38 (16)	C22—N21—C34—C31	178.80 (18)
N1—Zn1—N11—C20	91.15 (16)	Zn1—N21—C34—C31	−6.8 (2)
N21—Zn1—N11—C20	−121.0 (3)	C24—C33—C34—N21	−0.4 (3)
N30—Zn1—N11—C20	−76.63 (16)	C25—C33—C34—N21	179.21 (18)
Zn1—O11—C11—O12	−176.58 (17)	C24—C33—C34—C31	179.74 (18)
Zn1—O11—C11—C12	4.2 (2)	C25—C33—C34—C31	−0.7 (3)
C20—N11—C12—C13	−2.8 (3)	N30—C31—C34—N21	0.9 (3)
Zn1—N11—C12—C13	172.77 (14)	C32—C31—C34—N21	−178.43 (17)
C20—N11—C12—C11	176.96 (17)	N30—C31—C34—C33	−179.20 (17)
Zn1—N11—C12—C11	−7.47 (19)	C32—C31—C34—C33	1.4 (3)
O12—C11—C12—N11	−176.81 (18)	C50B—O50—C50A—N50	0.9 (7)
O11—C11—C12—N11	2.4 (2)	O50—C50A—N50—C50B	−1.0 (8)
O12—C11—C12—C13	2.9 (3)	O50—C50A—N50—C51A	−172.1 (4)
O11—C11—C12—C13	−177.81 (17)	O50—C50A—N50—C52A	−4.7 (5)
N11—C12—C13—C14	−175.18 (19)	O50—C50A—N50—C51B	171.8 (6)
C11—C12—C13—C14	5.1 (3)	C50A—N50—C50B—O50	1.0 (8)
N11—C12—C13—C18	3.0 (3)	C51A—N50—C50B—O50	46 (4)
C11—C12—C13—C18	−176.74 (18)	C52B—N50—C50B—O50	−174.9 (10)
C18—C13—C14—C15	0.1 (3)	C52A—N50—C50B—O50	177.4 (14)
C12—C13—C14—C15	178.2 (2)	C51B—N50—C50B—O50	−6.9 (16)
C13—C14—C15—C16	0.1 (4)	C50A—O50—C50B—N50	−1.1 (8)
C14—C15—C16—C17	0.3 (4)	C41—N40—C40—O40	−11.8 (7)
C15—C16—C17—C18	−0.8 (4)	C41^i—N40—C40—O40	168.2 (7)
C16—C17—C18—C19	−177.2 (2)	C42^i—N40—C40—O40	179.4 (5)
C16—C17—C18—C13	1.0 (4)	C42—N40—C40—O40	−0.6 (5)

Symmetry code: (i) −x+1, −y, −z+1.