Bis(9-amino-acridinium) bis-(pyridine-2,6-dicarboxyl-ato)zincate(II) trihydrate.

In the title compound, (C(13)H(11)N(2))(2)[Zn(C(7)H(3)NO(4))(2)]·3H(2)O, the Zn(II) ion is six-coordinated with the N(4)O(2) donor set being a distorted octa-hedron through two almost perpendicular (r.m.s. deviation of ligand atoms from the mean plane is 0.057 Å) tridentate pyridine-2,6-dicarboxyl-ate ligands [dihedral angle between the ligands = 86.06 (4)°]. The charge is compensated by two 9-amino-acridinium cations protonated on the ring N atom. A variety of inter-molecular contacts, such as ion-ion, N-H⋯O and O-H⋯O hydrogen bonds, and π-π stacking [centroid-centroid distances = 3.4907 (9)-4.1128 (8) Å], between cations and between anions, play important roles in the formation of the three-dimensional network.

Related literature

For the behaviour of 9-amino­acridine in coordination compounds see: Derikvand et al. (2010 ▶); Eshtiagh-Hosseini, Mirzaei, Eydizadeh et al. (2011 ▶). For a brief review of the pyridine­dicarboxyl­ate family of ligands, see: Mirzaei et al. (2011 ▶). For related structures, see: Aghabozorg et al. (2008 ▶); Derikvand et al. (2010 ▶); Eshtiagh-Hosseini, Yousefi, Mirzaei et al. (2010 ▶); Eshtiagh-Hosseini, Mirzaei, Eydizadeh et al. (2011 ▶); Eshtiagh-Hosseini, Mirzaei, Yousefi et al. (2011 ▶); Eshtiagh-Hosseini, Yousefi, Shafiee et al. (2010 ▶); Harrison et al. (2006 ▶); MacDonald et al. (2000 ▶); Park et al. (2007 ▶); Tabatabaee et al. (2009 ▶).

Experimental

Crystal data

(C13H11N2)2[Zn(C7H3NO4)2]·3H2O

M = 840.1

Triclinic,

a = 10.8763 (3) Å

b = 13.3802 (3) Å

c = 13.9920 (4) Å

α = 102.359 (2)°

β = 103.585 (2)°

γ = 105.137 (2)°

V = 1826.44 (8) Å3

Z = 2

Cu Kα radiation

μ = 1.57 mm−1

T = 293 K

0.1 × 0.1 × 0.1 mm

Data collection

Xcalibur Nova R CCD diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.786, T max = 1

18061 measured reflections

7540 independent reflections

6901 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.091

S = 1.03

7540 reflections

547 parameters

9 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.33 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812005764/mw2050sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005764/mw2050Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(C13H11N2)2[Zn(C7H3NO4)2]·3H2O	Z = 2
Mr = 840.1	F(000) = 868
Triclinic, P1	Dx = 1.528 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 10.8763 (3) Å	Cell parameters from 12486 reflections
b = 13.3802 (3) Å	θ = 3.4–75.7°
c = 13.9920 (4) Å	µ = 1.57 mm−1
α = 102.359 (2)°	T = 293 K
β = 103.585 (2)°	Prism, yellow
γ = 105.137 (2)°	0.1 × 0.1 × 0.1 mm
V = 1826.44 (8) Å3

Xcalibur Nova R CCD diffractometer	6901 reflections with I > 2σ(I)
ω scans	Rint = 0.023
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	θmax = 75.9°, θmin = 3.4°
Tmin = 0.786, Tmax = 1	h = −13→13
18061 measured reflections	k = −15→16
7540 independent reflections	l = −17→14

Refinement on F2	9 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.032	w = 1/[σ2(Fo2) + (0.0487P)2 + 0.2947P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.091	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.23 e Å−3
7540 reflections	Δρmin = −0.33 e Å−3
547 parameters

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.

	x	y	z	Uiso*/Ueq
Zn1	0.63843 (2)	0.757062 (15)	0.410290 (14)	0.04351 (8)
N1	0.56573 (12)	0.59395 (9)	0.37952 (8)	0.0339 (2)
N2	0.71182 (13)	0.91958 (9)	0.46845 (9)	0.0389 (2)
O1	0.79818 (13)	0.71221 (9)	0.51306 (9)	0.0519 (3)
O2	0.85048 (12)	0.56753 (10)	0.53916 (9)	0.0507 (3)
O7	0.53943 (14)	0.79380 (9)	0.52860 (9)	0.0514 (3)
O3	0.44757 (13)	0.71287 (9)	0.29115 (8)	0.0494 (3)
O5	0.75856 (15)	0.80175 (10)	0.31737 (9)	0.0560 (3)
O8	0.52661 (14)	0.93159 (10)	0.64241 (9)	0.0555 (3)
O6	0.90581 (15)	0.94355 (12)	0.30107 (11)	0.0626 (3)
C6	0.77303 (15)	0.61256 (12)	0.49985 (10)	0.0394 (3)
O4	0.26883 (14)	0.56750 (12)	0.19614 (11)	0.0649 (4)
C5	0.44187 (14)	0.54306 (11)	0.31581 (10)	0.0361 (3)
C14	0.57104 (17)	0.89226 (12)	0.57460 (10)	0.0414 (3)
C1	0.63454 (14)	0.54097 (11)	0.42913 (9)	0.0339 (3)
C2	0.57841 (16)	0.43143 (12)	0.41608 (11)	0.0397 (3)
H2	0.6266	0.3947	0.4504	0.048*
C12	0.67212 (16)	0.96945 (11)	0.54266 (10)	0.0397 (3)
C8	0.80023 (16)	0.97360 (12)	0.43042 (11)	0.0424 (3)
C7	0.37918 (16)	0.61393 (13)	0.26292 (11)	0.0436 (3)
C13	0.82615 (18)	0.90143 (13)	0.34225 (12)	0.0464 (3)
C11	0.7210 (2)	1.08125 (13)	0.58237 (12)	0.0503 (4)
H11	0.6917	1.1166	0.6328	0.06*
C3	0.44891 (17)	0.37785 (12)	0.35081 (12)	0.0441 (3)
H3	0.4088	0.3045	0.3415	0.053*
C4	0.37925 (16)	0.43381 (13)	0.29935 (11)	0.0432 (3)
H4	0.2925	0.3988	0.2549	0.052*
C9	0.8561 (2)	1.08539 (14)	0.46910 (14)	0.0544 (4)
H9	0.92	1.1236	0.4445	0.065*
C10	0.8145 (2)	1.13889 (14)	0.54521 (14)	0.0590 (4)
H10	0.8496	1.2139	0.5714	0.071*
H11A	−0.024 (3)	0.9280 (18)	−0.289 (2)	0.097 (10)*
H11B	−0.120 (2)	0.8243 (18)	−0.3509 (14)	0.076 (7)*
H9A	0.620 (2)	0.160 (2)	0.339 (2)	0.098 (9)*
H9B	0.749 (2)	0.2507 (17)	0.3719 (15)	0.073 (7)*
H10B	0.866 (3)	0.4303 (18)	0.480 (2)	0.101 (10)*
H10A	0.971 (2)	0.383 (2)	0.466 (2)	0.100 (10)*
N5	0.14315 (12)	0.60732 (10)	0.02168 (9)	0.0392 (2)
H5A	0.1775	0.5916	0.0761	0.047*
C28	0.10576 (13)	0.69735 (12)	0.03227 (11)	0.0372 (3)
C35	0.07187 (15)	0.56409 (13)	−0.16288 (11)	0.0420 (3)
N6	−0.01511 (16)	0.68630 (13)	−0.23874 (10)	0.0527 (3)
H6A	−0.0239	0.6464	−0.2986	0.063*
H6B	−0.0378	0.7437	−0.2329	0.063*
O11	−0.08439 (18)	0.86907 (13)	−0.28590 (11)	0.0707 (4)
C33	0.04982 (13)	0.72633 (12)	−0.05563 (11)	0.0381 (3)
C29	0.12309 (16)	0.76160 (14)	0.13159 (11)	0.0447 (3)
H29	0.1597	0.7421	0.189	0.054*
C32	0.01335 (15)	0.82143 (13)	−0.03963 (13)	0.0453 (3)
H32	−0.024	0.8421	−0.096	0.054*
C40	0.12830 (14)	0.54121 (12)	−0.07164 (11)	0.0396 (3)
C39	0.17044 (17)	0.44950 (13)	−0.07668 (13)	0.0484 (3)
H39	0.2069	0.4342	−0.0166	0.058*
C31	0.03218 (17)	0.88292 (14)	0.05684 (14)	0.0501 (4)
H31	0.0092	0.9458	0.0658	0.06*
C30	0.08634 (18)	0.85207 (15)	0.14347 (13)	0.0506 (4)
H30	0.097	0.8938	0.2091	0.061*
C34	0.03351 (14)	0.65921 (13)	−0.15526 (11)	0.0411 (3)
C37	0.1025 (2)	0.40490 (16)	−0.26117 (14)	0.0606 (4)
H37	0.0947	0.3594	−0.3242	0.073*
C36	0.0601 (2)	0.49258 (15)	−0.25790 (13)	0.0556 (4)
H36	0.0229	0.5057	−0.319	0.067*
C38	0.15744 (19)	0.38316 (15)	−0.17021 (16)	0.0573 (4)
H38	0.1855	0.3229	−0.1733	0.069*
C27	0.67785 (14)	0.08240 (13)	0.05915 (11)	0.0407 (3)
N3	0.66525 (13)	0.17238 (11)	0.11676 (9)	0.0439 (3)
H3A	0.6948	0.1886	0.1827	0.053*
N4	0.54649 (14)	0.10780 (11)	−0.19805 (9)	0.0443 (3)
H4B	0.5127	0.1504	−0.225	0.053*
H4A	0.5574	0.0536	−0.2366	0.053*
C23	0.65311 (16)	−0.03901 (13)	−0.10529 (13)	0.0453 (3)
H23	0.6285	−0.0575	−0.1767	0.054*
C21	0.58166 (13)	0.12563 (11)	−0.09735 (10)	0.0359 (3)
C20	0.56319 (14)	0.21631 (12)	−0.03328 (10)	0.0372 (3)
C15	0.60783 (15)	0.23768 (12)	0.07443 (11)	0.0408 (3)
C22	0.63677 (14)	0.05541 (12)	−0.04935 (11)	0.0375 (3)
C19	0.49415 (16)	0.28113 (13)	−0.07401 (12)	0.0446 (3)
H19	0.4608	0.2665	−0.1449	0.054*
C24	0.70489 (18)	−0.10350 (14)	−0.05529 (16)	0.0542 (4)
H24	0.714	−0.1659	−0.0929	0.065*
C25	0.74415 (17)	−0.07573 (16)	0.05241 (16)	0.0560 (4)
H25	0.7788	−0.1203	0.0855	0.067*
C26	0.73230 (16)	0.01550 (15)	0.10917 (14)	0.0512 (4)
H26	0.76	0.0337	0.1806	0.061*
C18	0.4757 (2)	0.36484 (15)	−0.01080 (15)	0.0546 (4)
H18	0.4294	0.4065	−0.0387	0.066*
C17	0.5266 (2)	0.38842 (15)	0.09648 (15)	0.0593 (4)
H17	0.5163	0.4473	0.1391	0.071*
C16	0.59065 (19)	0.32654 (15)	0.13869 (13)	0.0530 (4)
H16	0.6232	0.3426	0.2098	0.064*
O9	0.68488 (17)	0.20134 (14)	0.31754 (10)	0.0723 (4)
O10	0.88557 (15)	0.36441 (12)	0.47389 (13)	0.0688 (4)

	U11	U22	U33	U12	U13	U23
Zn1	0.06383 (14)	0.02983 (11)	0.03874 (11)	0.01721 (9)	0.01691 (9)	0.01034 (8)
N1	0.0428 (6)	0.0324 (5)	0.0296 (5)	0.0167 (5)	0.0112 (4)	0.0100 (4)
N2	0.0525 (7)	0.0318 (5)	0.0337 (5)	0.0155 (5)	0.0126 (5)	0.0110 (4)
O1	0.0553 (7)	0.0368 (5)	0.0517 (6)	0.0123 (5)	0.0013 (5)	0.0098 (5)
O2	0.0455 (6)	0.0502 (6)	0.0523 (6)	0.0214 (5)	0.0025 (5)	0.0135 (5)
O7	0.0785 (8)	0.0352 (5)	0.0488 (6)	0.0195 (5)	0.0323 (6)	0.0138 (4)
O3	0.0652 (7)	0.0457 (6)	0.0444 (5)	0.0271 (5)	0.0125 (5)	0.0210 (5)
O5	0.0796 (9)	0.0433 (6)	0.0523 (6)	0.0203 (6)	0.0349 (6)	0.0126 (5)
O8	0.0712 (8)	0.0487 (6)	0.0445 (6)	0.0158 (6)	0.0273 (6)	0.0037 (5)
O6	0.0747 (9)	0.0645 (8)	0.0610 (7)	0.0219 (7)	0.0370 (7)	0.0262 (6)
C6	0.0440 (7)	0.0399 (7)	0.0354 (6)	0.0174 (6)	0.0094 (5)	0.0117 (5)
O4	0.0563 (7)	0.0733 (9)	0.0597 (7)	0.0205 (6)	−0.0035 (6)	0.0330 (7)
C5	0.0422 (7)	0.0390 (7)	0.0300 (6)	0.0169 (6)	0.0106 (5)	0.0125 (5)
C14	0.0568 (8)	0.0387 (7)	0.0320 (6)	0.0197 (6)	0.0146 (6)	0.0110 (5)
C1	0.0417 (7)	0.0347 (6)	0.0299 (5)	0.0183 (5)	0.0118 (5)	0.0107 (5)
C2	0.0498 (8)	0.0378 (7)	0.0393 (6)	0.0219 (6)	0.0151 (6)	0.0157 (5)
C12	0.0522 (8)	0.0340 (7)	0.0318 (6)	0.0166 (6)	0.0094 (6)	0.0085 (5)
C8	0.0520 (8)	0.0388 (7)	0.0390 (7)	0.0159 (6)	0.0133 (6)	0.0160 (6)
C7	0.0498 (8)	0.0520 (9)	0.0372 (7)	0.0243 (7)	0.0126 (6)	0.0212 (6)
C13	0.0576 (9)	0.0475 (8)	0.0408 (7)	0.0204 (7)	0.0188 (7)	0.0186 (6)
C11	0.0702 (11)	0.0367 (7)	0.0395 (7)	0.0173 (7)	0.0145 (7)	0.0055 (6)
C3	0.0528 (8)	0.0340 (7)	0.0462 (7)	0.0125 (6)	0.0153 (6)	0.0150 (6)
C4	0.0427 (7)	0.0432 (8)	0.0395 (7)	0.0104 (6)	0.0085 (6)	0.0128 (6)
C9	0.0640 (10)	0.0408 (8)	0.0532 (9)	0.0069 (7)	0.0187 (8)	0.0153 (7)
C10	0.0770 (12)	0.0323 (7)	0.0558 (9)	0.0079 (8)	0.0163 (9)	0.0064 (7)
N5	0.0397 (6)	0.0423 (6)	0.0369 (6)	0.0156 (5)	0.0086 (5)	0.0153 (5)
C28	0.0324 (6)	0.0401 (7)	0.0391 (7)	0.0114 (5)	0.0099 (5)	0.0134 (5)
C35	0.0380 (7)	0.0430 (7)	0.0393 (7)	0.0092 (6)	0.0079 (5)	0.0101 (6)
N6	0.0608 (8)	0.0557 (8)	0.0366 (6)	0.0206 (7)	0.0037 (6)	0.0140 (6)
O11	0.0858 (10)	0.0624 (8)	0.0520 (7)	0.0127 (8)	0.0082 (7)	0.0216 (6)
C33	0.0315 (6)	0.0423 (7)	0.0397 (7)	0.0113 (5)	0.0083 (5)	0.0146 (6)
C29	0.0456 (8)	0.0514 (8)	0.0386 (7)	0.0173 (7)	0.0129 (6)	0.0146 (6)
C32	0.0385 (7)	0.0502 (8)	0.0515 (8)	0.0192 (6)	0.0113 (6)	0.0209 (7)
C40	0.0347 (6)	0.0394 (7)	0.0421 (7)	0.0094 (5)	0.0106 (5)	0.0114 (6)
C39	0.0472 (8)	0.0444 (8)	0.0557 (9)	0.0176 (7)	0.0154 (7)	0.0164 (7)
C31	0.0463 (8)	0.0492 (9)	0.0606 (9)	0.0230 (7)	0.0189 (7)	0.0159 (7)
C30	0.0523 (9)	0.0530 (9)	0.0471 (8)	0.0200 (7)	0.0183 (7)	0.0090 (7)
C34	0.0336 (6)	0.0462 (8)	0.0385 (7)	0.0087 (6)	0.0056 (5)	0.0141 (6)
C37	0.0655 (11)	0.0529 (10)	0.0512 (9)	0.0151 (8)	0.0160 (8)	−0.0014 (7)
C36	0.0596 (10)	0.0558 (10)	0.0413 (8)	0.0155 (8)	0.0088 (7)	0.0060 (7)
C38	0.0573 (10)	0.0433 (8)	0.0699 (11)	0.0185 (7)	0.0216 (8)	0.0089 (8)
C27	0.0317 (6)	0.0490 (8)	0.0420 (7)	0.0092 (6)	0.0112 (5)	0.0194 (6)
N3	0.0416 (6)	0.0543 (7)	0.0332 (5)	0.0112 (6)	0.0111 (5)	0.0134 (5)
N4	0.0589 (8)	0.0430 (6)	0.0347 (6)	0.0248 (6)	0.0132 (5)	0.0101 (5)
C23	0.0426 (7)	0.0415 (7)	0.0522 (8)	0.0150 (6)	0.0138 (6)	0.0139 (6)
C21	0.0344 (6)	0.0363 (6)	0.0360 (6)	0.0099 (5)	0.0119 (5)	0.0099 (5)
C20	0.0358 (6)	0.0381 (7)	0.0371 (6)	0.0102 (5)	0.0138 (5)	0.0094 (5)
C15	0.0380 (7)	0.0449 (8)	0.0374 (7)	0.0086 (6)	0.0152 (5)	0.0099 (6)
C22	0.0331 (6)	0.0389 (7)	0.0406 (7)	0.0100 (5)	0.0118 (5)	0.0136 (5)
C19	0.0494 (8)	0.0428 (8)	0.0456 (7)	0.0176 (6)	0.0179 (6)	0.0143 (6)
C24	0.0473 (8)	0.0433 (8)	0.0768 (11)	0.0182 (7)	0.0197 (8)	0.0222 (8)
C25	0.0417 (8)	0.0595 (10)	0.0783 (12)	0.0185 (7)	0.0175 (8)	0.0418 (9)
C26	0.0386 (7)	0.0645 (10)	0.0565 (9)	0.0142 (7)	0.0137 (7)	0.0343 (8)
C18	0.0624 (10)	0.0467 (9)	0.0655 (10)	0.0259 (8)	0.0292 (8)	0.0177 (8)
C17	0.0756 (12)	0.0459 (9)	0.0629 (10)	0.0222 (8)	0.0386 (9)	0.0069 (7)
C16	0.0615 (10)	0.0520 (9)	0.0418 (7)	0.0120 (8)	0.0241 (7)	0.0056 (7)
O9	0.0747 (9)	0.0853 (10)	0.0369 (6)	−0.0009 (8)	0.0153 (6)	0.0135 (6)
O10	0.0567 (8)	0.0507 (7)	0.0871 (10)	0.0111 (6)	0.0171 (7)	0.0099 (7)

Zn1—N2	2.0146 (12)	C33—C32	1.418 (2)
Zn1—N1	2.0274 (11)	C33—C34	1.430 (2)
Zn1—O5	2.1162 (12)	C29—C30	1.360 (2)
Zn1—O3	2.1793 (12)	C29—H29	0.93
Zn1—O7	2.2151 (11)	C32—C31	1.359 (2)
Zn1—O1	2.2775 (12)	C32—H32	0.93
N1—C5	1.3304 (19)	C40—C39	1.412 (2)
N1—C1	1.3372 (17)	C39—C38	1.368 (3)
N2—C8	1.331 (2)	C39—H39	0.93
N2—C12	1.3321 (19)	C31—C30	1.412 (2)
O1—C6	1.2518 (19)	C31—H31	0.93
O2—C6	1.2508 (18)	C30—H30	0.93
O7—C14	1.2507 (19)	C37—C36	1.364 (3)
O3—C7	1.259 (2)	C37—C38	1.398 (3)
O5—C13	1.269 (2)	C37—H37	0.93
O8—C14	1.2430 (19)	C36—H36	0.93
O6—C13	1.232 (2)	C38—H38	0.93
C6—C1	1.519 (2)	C27—N3	1.357 (2)
O4—C7	1.239 (2)	C27—C26	1.411 (2)
C5—C4	1.384 (2)	C27—C22	1.413 (2)
C5—C7	1.5207 (18)	N3—C15	1.355 (2)
C14—C12	1.520 (2)	N3—H3A	0.86
C1—C2	1.386 (2)	N4—C21	1.3206 (18)
C2—C3	1.386 (2)	N4—H4B	0.86
C2—H2	0.93	N4—H4A	0.86
C12—C11	1.385 (2)	C23—C24	1.370 (2)
C8—C9	1.387 (2)	C23—C22	1.414 (2)
C8—C13	1.526 (2)	C23—H23	0.93
C11—C10	1.382 (3)	C21—C20	1.4361 (19)
C11—H11	0.93	C21—C22	1.4382 (19)
C3—C4	1.387 (2)	C20—C15	1.4100 (19)
C3—H3	0.93	C20—C19	1.411 (2)
C4—H4	0.93	C15—C16	1.412 (2)
C9—C10	1.386 (3)	C19—C18	1.361 (2)
C9—H9	0.93	C19—H19	0.93
C10—H10	0.93	C24—C25	1.402 (3)
N5—C40	1.359 (2)	C24—H24	0.93
N5—C28	1.3588 (19)	C25—C26	1.361 (3)
N5—H5A	0.86	C25—H25	0.93
C28—C29	1.409 (2)	C26—H26	0.93
C28—C33	1.4173 (18)	C18—C17	1.405 (3)
C35—C40	1.413 (2)	C18—H18	0.93
C35—C36	1.418 (2)	C17—C16	1.355 (3)
C35—C34	1.430 (2)	C17—H17	0.93
N6—C34	1.3291 (19)	C16—H16	0.93
N6—H6A	0.86	O9—H9A	0.928 (17)
N6—H6B	0.86	O9—H9B	0.890 (16)
O11—H11A	0.900 (17)	O10—H10B	0.948 (17)
O11—H11B	0.903 (16)	O10—H10A	0.940 (17)
N2—Zn1—N1	169.12 (4)	C28—C33—C32	117.75 (14)
N2—Zn1—O5	77.62 (5)	C28—C33—C34	118.85 (13)
N1—Zn1—O5	111.49 (5)	C32—C33—C34	123.40 (13)
N2—Zn1—O3	108.72 (5)	C30—C29—C28	120.01 (14)
N1—Zn1—O3	77.03 (4)	C30—C29—H29	120
O5—Zn1—O3	95.55 (5)	C28—C29—H29	120
N2—Zn1—O7	75.67 (5)	C31—C32—C33	121.01 (14)
N1—Zn1—O7	95.48 (4)	C31—C32—H32	119.5
O5—Zn1—O7	153.00 (4)	C33—C32—H32	119.5
O3—Zn1—O7	89.34 (5)	N5—C40—C39	119.33 (13)
N2—Zn1—O1	99.73 (5)	N5—C40—C35	120.47 (13)
N1—Zn1—O1	74.39 (4)	C39—C40—C35	120.20 (14)
O5—Zn1—O1	93.41 (5)	C38—C39—C40	119.78 (16)
O3—Zn1—O1	151.38 (4)	C38—C39—H39	120.1
O7—Zn1—O1	94.87 (5)	C40—C39—H39	120.1
C5—N1—C1	121.08 (12)	C32—C31—C30	120.49 (15)
C5—N1—Zn1	117.51 (9)	C32—C31—H31	119.8
C1—N1—Zn1	121.10 (10)	C30—C31—H31	119.8
C8—N2—C12	122.19 (13)	C29—C30—C31	120.39 (15)
C8—N2—Zn1	117.72 (10)	C29—C30—H30	119.8
C12—N2—Zn1	120.10 (10)	C31—C30—H30	119.8
C6—O1—Zn1	114.35 (10)	N6—C34—C35	121.08 (15)
C14—O7—Zn1	114.84 (10)	N6—C34—C33	120.02 (15)
C7—O3—Zn1	114.70 (9)	C35—C34—C33	118.90 (13)
C13—O5—Zn1	116.07 (10)	C36—C37—C38	120.31 (17)
O2—C6—O1	126.28 (15)	C36—C37—H37	119.8
O2—C6—C1	117.83 (13)	C38—C37—H37	119.8
O1—C6—C1	115.89 (12)	C37—C36—C35	121.13 (16)
N1—C5—C4	121.23 (12)	C37—C36—H36	119.4
N1—C5—C7	114.56 (13)	C35—C36—H36	119.4
C4—C5—C7	124.19 (13)	C39—C38—C37	120.76 (17)
O8—C14—O7	125.98 (15)	C39—C38—H38	119.6
O8—C14—C12	118.02 (14)	C37—C38—H38	119.6
O7—C14—C12	116.00 (13)	N3—C27—C26	119.00 (14)
N1—C1—C2	120.86 (13)	N3—C27—C22	120.76 (13)
N1—C1—C6	113.66 (12)	C26—C27—C22	120.24 (15)
C2—C1—C6	125.46 (12)	C15—N3—C27	122.52 (12)
C3—C2—C1	118.57 (12)	C15—N3—H3A	118.7
C3—C2—H2	120.7	C27—N3—H3A	118.7
C1—C2—H2	120.7	C21—N4—H4B	120
N2—C12—C11	120.49 (15)	C21—N4—H4A	120
N2—C12—C14	113.39 (12)	H4B—N4—H4A	120
C11—C12—C14	126.11 (14)	C24—C23—C22	120.64 (16)
N2—C8—C9	120.14 (15)	C24—C23—H23	119.7
N2—C8—C13	113.60 (13)	C22—C23—H23	119.7
C9—C8—C13	126.22 (15)	N4—C21—C20	119.76 (13)
O4—C7—O3	127.83 (14)	N4—C21—C22	121.71 (13)
O4—C7—C5	116.49 (15)	C20—C21—C22	118.53 (12)
O3—C7—C5	115.66 (13)	C15—C20—C19	118.30 (13)
O6—C13—O5	126.46 (16)	C15—C20—C21	119.08 (13)
O6—C13—C8	118.82 (15)	C19—C20—C21	122.49 (13)
O5—C13—C8	114.70 (14)	N3—C15—C20	120.40 (14)
C10—C11—C12	118.33 (16)	N3—C15—C16	119.69 (14)
C10—C11—H11	120.8	C20—C15—C16	119.90 (15)
C12—C11—H11	120.8	C27—C22—C23	118.21 (13)
C2—C3—C4	119.85 (14)	C27—C22—C21	118.51 (13)
C2—C3—H3	120.1	C23—C22—C21	123.27 (13)
C4—C3—H3	120.1	C18—C19—C20	120.83 (15)
C5—C4—C3	118.40 (14)	C18—C19—H19	119.6
C5—C4—H4	120.8	C20—C19—H19	119.6
C3—C4—H4	120.8	C23—C24—C25	120.27 (17)
C10—C9—C8	118.51 (16)	C23—C24—H24	119.9
C10—C9—H9	120.7	C25—C24—H24	119.9
C8—C9—H9	120.7	C26—C25—C24	120.93 (15)
C11—C10—C9	120.30 (16)	C26—C25—H25	119.5
C11—C10—H10	119.9	C24—C25—H25	119.5
C9—C10—H10	119.9	C25—C26—C27	119.70 (16)
C40—N5—C28	122.46 (12)	C25—C26—H26	120.1
C40—N5—H5A	118.8	C27—C26—H26	120.1
C28—N5—H5A	118.8	C19—C18—C17	120.14 (17)
N5—C28—C29	119.30 (12)	C19—C18—H18	119.9
N5—C28—C33	120.36 (13)	C17—C18—H18	119.9
C29—C28—C33	120.34 (13)	C16—C17—C18	120.86 (16)
C40—C35—C36	117.82 (15)	C16—C17—H17	119.6
C40—C35—C34	118.93 (14)	C18—C17—H17	119.6
C36—C35—C34	123.22 (14)	C17—C16—C15	119.84 (16)
C34—N6—H6A	120	C17—C16—H16	120.1
C34—N6—H6B	120	C15—C16—H16	120.1
H6A—N6—H6B	120	H9A—O9—H9B	110 (2)
H11A—O11—H11B	105 (2)	H10B—O10—H10A	102 (2)
N2—Zn1—N1—C5	116.6 (3)	N2—C8—C13—O5	1.1 (2)
O5—Zn1—N1—C5	−97.47 (10)	C9—C8—C13—O5	−176.85 (16)
O3—Zn1—N1—C5	−6.56 (9)	N2—C12—C11—C10	−1.9 (2)
O7—Zn1—N1—C5	81.49 (10)	C14—C12—C11—C10	179.04 (15)
O1—Zn1—N1—C5	175.03 (10)	C1—C2—C3—C4	0.8 (2)
N2—Zn1—N1—C1	−57.0 (3)	N1—C5—C4—C3	−0.2 (2)
O5—Zn1—N1—C1	88.95 (10)	C7—C5—C4—C3	178.49 (14)
O3—Zn1—N1—C1	179.86 (11)	C2—C3—C4—C5	−0.5 (2)
O7—Zn1—N1—C1	−92.09 (10)	N2—C8—C9—C10	−2.0 (3)
O1—Zn1—N1—C1	1.45 (10)	C13—C8—C9—C10	175.78 (16)
N1—Zn1—N2—C8	143.5 (2)	C12—C11—C10—C9	0.9 (3)
O5—Zn1—N2—C8	−4.29 (11)	C8—C9—C10—C11	1.0 (3)
O3—Zn1—N2—C8	−96.02 (11)	C40—N5—C28—C29	179.43 (13)
O7—Zn1—N2—C8	179.67 (12)	C40—N5—C28—C33	−0.5 (2)
O1—Zn1—N2—C8	87.09 (11)	N5—C28—C33—C32	−179.70 (13)
N1—Zn1—N2—C12	−36.3 (3)	C29—C28—C33—C32	0.3 (2)
O5—Zn1—N2—C12	175.94 (12)	N5—C28—C33—C34	0.0 (2)
O3—Zn1—N2—C12	84.21 (11)	C29—C28—C33—C34	−179.92 (13)
O7—Zn1—N2—C12	−0.10 (11)	N5—C28—C29—C30	179.90 (15)
O1—Zn1—N2—C12	−92.68 (11)	C33—C28—C29—C30	−0.1 (2)
N2—Zn1—O1—C6	174.45 (11)	C28—C33—C32—C31	0.3 (2)
N1—Zn1—O1—C6	3.84 (11)	C34—C33—C32—C31	−179.37 (15)
O5—Zn1—O1—C6	−107.54 (12)	C28—N5—C40—C39	179.49 (14)
O3—Zn1—O1—C6	0.61 (18)	C28—N5—C40—C35	−0.2 (2)
O7—Zn1—O1—C6	98.19 (12)	C36—C35—C40—N5	179.45 (15)
N2—Zn1—O7—C14	0.37 (11)	C34—C35—C40—N5	1.4 (2)
N1—Zn1—O7—C14	173.94 (11)	C36—C35—C40—C39	−0.2 (2)
O5—Zn1—O7—C14	−8.18 (19)	C34—C35—C40—C39	−178.29 (14)
O3—Zn1—O7—C14	−109.16 (12)	N5—C40—C39—C38	−179.20 (15)
O1—Zn1—O7—C14	99.19 (12)	C35—C40—C39—C38	0.5 (2)
N2—Zn1—O3—C7	−166.74 (11)	C33—C32—C31—C30	−1.2 (3)
N1—Zn1—O3—C7	3.66 (11)	C28—C29—C30—C31	−0.7 (3)
O5—Zn1—O3—C7	114.47 (11)	C32—C31—C30—C29	1.4 (3)
O7—Zn1—O3—C7	−92.12 (11)	C40—C35—C34—N6	177.36 (14)
O1—Zn1—O3—C7	6.85 (17)	C36—C35—C34—N6	−0.6 (2)
N2—Zn1—O5—C13	4.95 (12)	C40—C35—C34—C33	−1.8 (2)
N1—Zn1—O5—C13	−168.84 (12)	C36—C35—C34—C33	−179.79 (15)
O3—Zn1—O5—C13	112.94 (13)	C28—C33—C34—N6	−178.06 (14)
O7—Zn1—O5—C13	13.4 (2)	C32—C33—C34—N6	1.7 (2)
O1—Zn1—O5—C13	−94.27 (13)	C28—C33—C34—C35	1.2 (2)
Zn1—O1—C6—O2	172.37 (13)	C32—C33—C34—C35	−179.13 (14)
Zn1—O1—C6—C1	−7.72 (16)	C38—C37—C36—C35	0.7 (3)
C1—N1—C5—C4	0.7 (2)	C40—C35—C36—C37	−0.3 (3)
Zn1—N1—C5—C4	−172.91 (11)	C34—C35—C36—C37	177.63 (17)
C1—N1—C5—C7	−178.13 (12)	C40—C39—C38—C37	−0.2 (3)
Zn1—N1—C5—C7	8.29 (15)	C36—C37—C38—C39	−0.4 (3)
Zn1—O7—C14—O8	178.80 (13)	C26—C27—N3—C15	−176.61 (14)
Zn1—O7—C14—C12	−0.54 (17)	C22—C27—N3—C15	3.1 (2)
C5—N1—C1—C2	−0.41 (19)	N4—C21—C20—C15	−176.62 (14)
Zn1—N1—C1—C2	172.94 (10)	C22—C21—C20—C15	4.3 (2)
C5—N1—C1—C6	−178.99 (11)	N4—C21—C20—C19	7.6 (2)
Zn1—N1—C1—C6	−5.63 (15)	C22—C21—C20—C19	−171.54 (13)
O2—C6—C1—N1	−171.15 (13)	C27—N3—C15—C20	−2.7 (2)
O1—C6—C1—N1	8.94 (18)	C27—N3—C15—C16	176.26 (14)
O2—C6—C1—C2	10.4 (2)	C19—C20—C15—N3	174.83 (14)
O1—C6—C1—C2	−169.56 (14)	C21—C20—C15—N3	−1.1 (2)
N1—C1—C2—C3	−0.3 (2)	C19—C20—C15—C16	−4.1 (2)
C6—C1—C2—C3	178.07 (13)	C21—C20—C15—C16	179.95 (14)
C8—N2—C12—C11	0.9 (2)	N3—C27—C22—C23	179.63 (13)
Zn1—N2—C12—C11	−179.33 (12)	C26—C27—C22—C23	−0.6 (2)
C8—N2—C12—C14	−179.89 (13)	N3—C27—C22—C21	0.2 (2)
Zn1—N2—C12—C14	−0.14 (16)	C26—C27—C22—C21	179.93 (13)
O8—C14—C12—N2	−178.93 (14)	C24—C23—C22—C27	1.3 (2)
O7—C14—C12—N2	0.47 (19)	C24—C23—C22—C21	−179.26 (15)
O8—C14—C12—C11	0.2 (2)	N4—C21—C22—C27	177.11 (13)
O7—C14—C12—C11	179.61 (15)	C20—C21—C22—C27	−3.8 (2)
C12—N2—C8—C9	1.1 (2)	N4—C21—C22—C23	−2.3 (2)
Zn1—N2—C8—C9	−178.67 (12)	C20—C21—C22—C23	176.81 (13)
C12—N2—C8—C13	−176.99 (13)	C15—C20—C19—C18	2.5 (2)
Zn1—N2—C8—C13	3.25 (17)	C21—C20—C19—C18	178.36 (15)
Zn1—O3—C7—O4	−178.96 (15)	C22—C23—C24—C25	−0.9 (3)
Zn1—O3—C7—C5	−0.54 (17)	C23—C24—C25—C26	−0.3 (3)
N1—C5—C7—O4	173.70 (14)	C24—C25—C26—C27	1.0 (2)
C4—C5—C7—O4	−5.1 (2)	N3—C27—C26—C25	179.23 (14)
N1—C5—C7—O3	−4.91 (19)	C22—C27—C26—C25	−0.5 (2)
C4—C5—C7—O3	176.33 (14)	C20—C19—C18—C17	0.6 (3)
Zn1—O5—C13—O6	177.06 (14)	C19—C18—C17—C16	−2.2 (3)
Zn1—O5—C13—C8	−4.65 (18)	C18—C17—C16—C15	0.6 (3)
N2—C8—C13—O6	179.52 (15)	N3—C15—C16—C17	−176.35 (16)
C9—C8—C13—O6	1.6 (3)	C20—C15—C16—C17	2.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O9	0.86	1.89	2.7013 (18)	157
N4—H4A···O8i	0.86	1.98	2.8005 (18)	160
N4—H4B···O3ii	0.86	2.21	2.9589 (19)	145
N5—H5A···O4	0.86	1.88	2.7351 (19)	174
N6—H6A···O2iii	0.86	2.21	2.9763 (18)	148
N6—H6B···O11	0.86	2.10	2.899 (2)	154
O9—H9A···O8iv	0.93 (3)	1.85 (3)	2.768 (2)	170 (2)
O9—H9B···O10	0.89 (2)	1.86 (2)	2.745 (2)	173 (2)
O10—H10A···O2v	0.94 (2)	1.91 (2)	2.838 (2)	175 (2)
O10—H10B···O2	0.95 (3)	1.91 (3)	2.830 (2)	161 (2)
O11—H11A···O6vi	0.90 (3)	1.93 (3)	2.825 (2)	176 (3)
O11—H11B···O1iii	0.90 (2)	1.99 (2)	2.8869 (19)	174 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O9	0.86	1.89	2.7013 (18)	157
N4—H4A⋯O8i	0.86	1.98	2.8005 (18)	160
N4—H4B⋯O3ii	0.86	2.21	2.9589 (19)	145
N5—H5A⋯O4	0.86	1.88	2.7351 (19)	174
N6—H6A⋯O2iii	0.86	2.21	2.9763 (18)	148
N6—H6B⋯O11	0.86	2.10	2.899 (2)	154
O9—H9A⋯O8iv	0.93 (3)	1.85 (3)	2.768 (2)	170 (2)
O9—H9B⋯O10	0.89 (2)	1.86 (2)	2.745 (2)	173 (2)
O10—H10A⋯O2v	0.94 (2)	1.91 (2)	2.838 (2)	175 (2)
O10—H10B⋯O2	0.95 (3)	1.91 (3)	2.830 (2)	161 (2)
O11—H11A⋯O6vi	0.90 (3)	1.93 (3)	2.825 (2)	176 (3)
O11—H11B⋯O1iii	0.90 (2)	1.99 (2)	2.8869 (19)	174 (2)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .