catena-Poly[[[diaqua-(1,10-phenanthroline-κ(2)N,N')zinc]-μ-4,4'-bipyridine-κ(2)N:N'] dinitrate 4,4'-bipyridine hemisolvate monohydrate].

In the title compound, [Zn(C(10)H(8)N(2))(C(12)H(8)N(2))(H(2)O)(2)](NO(3))(2)·0.5C(10)H(8)N(2)·H(2)O, the Zn(II) atom is coordinated in a distorted octa-hedral geometry by two N atoms from two 4,4'-bipyridine (4,4'-bipy) ligands, two N atoms from a chelating 1,10-phenanthroline ligand and two O atoms from two mutually cis water mol-ecules. The 4,4'-bipy ligands bridge the Zn(II) atoms into a chain structure along [100]. The uncoordinated 4,4'-bipy mol-ecule lies on an inversion center. O-H⋯O and O-H⋯N hydrogen bonds connect the cationic chains, the nitrate anions, the uncoordinated 4,4'-bipy mol-ecules and the water mol-ecules into tow-dimensional networks.

Related literature

For background to metal complexes of n class="Chemical">1,10-phenanthroline and its derivatives in biological systems, see: Rama Krishna et al. (2000 ▶); Sastri et al. (2003 ▶). For related structures, see: Bai et al. (2009 ▶); Blake et al. (1998 ▶); Boag et al. (1999 ▶); Carlucci et al. (1997 ▶); Chen et al. (2006 ▶); Du & Li (2007 ▶); Ma et al. (2006 ▶); Xiong et al. (1999 ▶); Zhang et al. (2009 ▶); Zhang & Janiak (2001 ▶).

Experimental

Crystal data

[Zn(C10n class="Species">H8N2)(C12H8N2)(H2O)2](NO3)2·0.5C10H8N2·H2O

M = 657.94

Monoclinic,

a = 11.3910 (11) Å

b = 13.0561 (13) Å

c = 19.8509 (18) Å

β = 103.487 (1)°

V = 2870.9 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.92 mm−1

T = 298 K

0.35 × 0.31 × 0.18 mm

Data collection

Bruker APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.739, T max = 0.852

14110 measured reflections

5072 independent reflections

3309 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.132

S = 1.03

5072 reflections

397 parameters

H-atom parameters constrained

Δρmax = 0.81 e Å−3

Δρmin = −0.42 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812036318/hy2580sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036318/hy2580Isup2.hkl

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

[Zn(C10H8N2)(C12H8N2)(H2O)2](NO3)2·0.5C10H8N2·H2O	F(000) = 1356
Mr = 657.94	Dx = 1.522 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3365 reflections
a = 11.3910 (11) Å	θ = 2.4–22.8°
b = 13.0561 (13) Å	µ = 0.92 mm−1
c = 19.8509 (18) Å	T = 298 K
β = 103.487 (1)°	Block, yellow
V = 2870.9 (5) Å3	0.35 × 0.31 × 0.18 mm
Z = 4

Bruker APEX CCD diffractometer	5072 independent reflections
Radiation source: fine-focus sealed tube	3309 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
φ and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −13→13
Tmin = 0.739, Tmax = 0.852	k = −15→10
14110 measured reflections	l = −22→23

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0523P)2 + 3.4384P] where P = (Fo2 + 2Fc2)/3
5072 reflections	(Δ/σ)max = 0.001
397 parameters	Δρmax = 0.81 e Å−3
0 restraints	Δρmin = −0.42 e Å−3

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.

	x	y	z	Uiso*/Ueq
Zn1	0.79800 (4)	0.79895 (4)	0.38707 (2)	0.03238 (17)
N1	0.8386 (3)	0.7200 (3)	0.48637 (17)	0.0397 (9)
N2	0.7735 (3)	0.6396 (3)	0.35719 (18)	0.0373 (8)
N3	−0.0104 (3)	0.7983 (3)	0.38878 (17)	0.0363 (8)
N4	0.6095 (3)	0.8140 (3)	0.38381 (17)	0.0337 (8)
N5	0.6004 (4)	0.9079 (4)	0.1717 (2)	0.0576 (11)
N6	1.0006 (4)	0.0462 (4)	0.3071 (3)	0.0659 (13)
N7	0.3949 (6)	0.6227 (5)	0.1489 (3)	0.0878 (16)
O1	0.9895 (4)	0.0465 (3)	0.3673 (2)	0.0837 (13)
O2	1.0852 (4)	0.0946 (4)	0.2944 (3)	0.1126 (17)
O3	0.9290 (5)	0.0019 (4)	0.2633 (2)	0.120 (2)
O4	0.4873 (5)	0.6379 (5)	0.1878 (3)	0.147 (3)
O5	0.2995 (7)	0.6575 (6)	0.1641 (4)	0.183 (3)
O6	0.3835 (4)	0.5724 (3)	0.0954 (2)	0.0823 (13)
O7	0.8234 (2)	0.9520 (2)	0.42605 (15)	0.0448 (8)
H7C	0.8747	0.9816	0.4078	0.054*
H7D	0.7603	0.9890	0.4194	0.054*
O8	0.7743 (2)	0.8506 (2)	0.28439 (14)	0.0476 (8)
H8C	0.7144	0.8618	0.2507	0.057*
H8D	0.8287	0.8944	0.2826	0.057*
O9	0.3302 (5)	0.0820 (4)	0.4013 (2)	0.1229 (18)
H9C	0.2611	0.0847	0.3736	0.148*
H9D	0.3830	0.0968	0.3789	0.148*
C1	0.8733 (4)	0.7593 (4)	0.5490 (2)	0.0553 (13)
H1	0.8777	0.8301	0.5541	0.066*
C2	0.9036 (5)	0.6974 (6)	0.6082 (3)	0.0771 (18)
H2	0.9285	0.7271	0.6518	0.093*
C3	0.8967 (5)	0.5944 (6)	0.6017 (3)	0.0782 (18)
H3	0.9166	0.5530	0.6409	0.094*
C4	0.8602 (4)	0.5505 (5)	0.5369 (3)	0.0611 (14)
C5	0.8325 (4)	0.6162 (4)	0.4794 (2)	0.0423 (11)
C6	0.7960 (4)	0.5739 (4)	0.4114 (2)	0.0424 (11)
C7	0.7839 (4)	0.4668 (4)	0.4024 (3)	0.0593 (14)
C8	0.7443 (6)	0.4308 (5)	0.3349 (3)	0.0785 (18)
H8	0.7346	0.3608	0.3266	0.094*
C9	0.7204 (6)	0.4973 (5)	0.2817 (3)	0.0773 (17)
H9	0.6925	0.4737	0.2366	0.093*
C10	0.7374 (4)	0.6014 (4)	0.2944 (3)	0.0510 (12)
H10	0.7226	0.6461	0.2569	0.061*
C11	0.8484 (5)	0.4422 (5)	0.5253 (4)	0.0796 (18)
H11	0.8674	0.3981	0.5630	0.096*
C12	0.8109 (6)	0.4029 (5)	0.4618 (4)	0.0801 (18)
H12	0.8023	0.3323	0.4564	0.096*
C13	0.0304 (4)	0.7574 (4)	0.3374 (2)	0.0434 (11)
H13	−0.0247	0.7248	0.3019	0.052*
C14	0.1494 (4)	0.7604 (4)	0.3336 (2)	0.0442 (11)
H14	0.1729	0.7300	0.2965	0.053*
C15	0.2337 (3)	0.8084 (3)	0.3850 (2)	0.0315 (9)
C16	0.1911 (3)	0.8501 (4)	0.4388 (2)	0.0426 (11)
H16	0.2441	0.8832	0.4750	0.051*
C17	0.0713 (4)	0.8429 (4)	0.4390 (2)	0.0428 (11)
H17	0.0457	0.8708	0.4762	0.051*
C18	0.5701 (3)	0.8456 (3)	0.4383 (2)	0.0366 (10)
H18	0.6270	0.8680	0.4770	0.044*
C19	0.4508 (3)	0.8473 (3)	0.4409 (2)	0.0350 (10)
H19	0.4284	0.8705	0.4804	0.042*
C20	0.3639 (3)	0.8139 (3)	0.3839 (2)	0.0308 (9)
C21	0.4049 (3)	0.7837 (3)	0.3263 (2)	0.0360 (10)
H21	0.3501	0.7623	0.2864	0.043*
C22	0.5252 (3)	0.7853 (3)	0.3281 (2)	0.0358 (10)
H22	0.5499	0.7655	0.2886	0.043*
C23	0.5748 (6)	1.0034 (5)	0.1576 (3)	0.087 (2)
H23	0.5841	1.0487	0.1946	0.105*
C24	0.5350 (6)	1.0426 (4)	0.0921 (3)	0.082 (2)
H24	0.5182	1.1122	0.0860	0.098*
C25	0.5200 (4)	0.9801 (3)	0.0361 (2)	0.0395 (10)
C26	0.5451 (6)	0.8796 (4)	0.0508 (3)	0.0810 (19)
H26	0.5353	0.8320	0.0151	0.097*
C27	0.5849 (6)	0.8484 (5)	0.1182 (3)	0.086 (2)
H27	0.6020	0.7792	0.1261	0.103*

	U11	U22	U33	U12	U13	U23
Zn1	0.0222 (2)	0.0411 (3)	0.0338 (3)	0.0005 (2)	0.00634 (18)	0.0014 (2)
N1	0.0302 (18)	0.053 (3)	0.035 (2)	0.0011 (17)	0.0064 (15)	0.0012 (18)
N2	0.0286 (18)	0.039 (2)	0.044 (2)	0.0014 (16)	0.0082 (15)	−0.0020 (19)
N3	0.0218 (16)	0.050 (2)	0.0361 (19)	0.0012 (16)	0.0058 (15)	0.0011 (18)
N4	0.0244 (17)	0.042 (2)	0.0363 (19)	0.0003 (15)	0.0103 (15)	0.0024 (16)
N5	0.059 (3)	0.061 (3)	0.046 (3)	0.001 (2)	−0.001 (2)	0.009 (2)
N6	0.067 (3)	0.067 (3)	0.068 (3)	−0.014 (3)	0.024 (3)	0.014 (3)
N7	0.095 (5)	0.088 (4)	0.081 (4)	−0.027 (4)	0.022 (4)	−0.007 (4)
O1	0.085 (3)	0.093 (3)	0.078 (3)	−0.041 (2)	0.027 (2)	0.001 (2)
O2	0.106 (4)	0.127 (4)	0.118 (4)	−0.047 (3)	0.052 (3)	0.014 (3)
O3	0.137 (4)	0.156 (5)	0.063 (3)	−0.090 (4)	0.015 (3)	−0.010 (3)
O4	0.119 (4)	0.205 (7)	0.092 (4)	−0.058 (4)	−0.026 (3)	−0.014 (4)
O5	0.163 (7)	0.150 (6)	0.252 (9)	−0.036 (5)	0.081 (6)	−0.076 (6)
O6	0.100 (3)	0.084 (3)	0.068 (3)	−0.027 (2)	0.031 (2)	−0.027 (2)
O7	0.0361 (16)	0.0462 (19)	0.0530 (19)	−0.0017 (14)	0.0124 (14)	−0.0019 (16)
O8	0.0310 (16)	0.071 (2)	0.0373 (17)	−0.0045 (15)	0.0010 (13)	0.0162 (16)
O9	0.142 (5)	0.132 (5)	0.089 (4)	0.002 (4)	0.014 (3)	−0.008 (3)
C1	0.053 (3)	0.070 (4)	0.041 (3)	−0.004 (3)	0.007 (2)	−0.005 (3)
C2	0.084 (4)	0.112 (6)	0.030 (3)	0.008 (4)	0.002 (3)	0.005 (3)
C3	0.088 (5)	0.093 (5)	0.051 (4)	0.012 (4)	0.010 (3)	0.030 (4)
C4	0.056 (3)	0.073 (4)	0.054 (3)	0.011 (3)	0.012 (3)	0.023 (3)
C5	0.032 (2)	0.048 (3)	0.047 (3)	0.006 (2)	0.010 (2)	0.011 (2)
C6	0.029 (2)	0.046 (3)	0.052 (3)	0.005 (2)	0.009 (2)	0.000 (2)
C7	0.056 (3)	0.044 (3)	0.079 (4)	0.003 (2)	0.018 (3)	0.008 (3)
C8	0.103 (5)	0.042 (4)	0.086 (5)	−0.008 (3)	0.014 (4)	−0.015 (3)
C9	0.106 (5)	0.054 (4)	0.067 (4)	−0.010 (3)	0.010 (3)	−0.013 (3)
C10	0.053 (3)	0.049 (3)	0.049 (3)	−0.002 (2)	0.007 (2)	−0.004 (3)
C11	0.085 (4)	0.067 (4)	0.087 (5)	0.022 (3)	0.019 (4)	0.044 (4)
C12	0.099 (5)	0.049 (4)	0.091 (5)	0.008 (3)	0.020 (4)	0.023 (4)
C13	0.028 (2)	0.061 (3)	0.039 (2)	−0.005 (2)	0.0034 (19)	−0.009 (2)
C14	0.029 (2)	0.065 (3)	0.041 (3)	−0.002 (2)	0.0120 (19)	−0.010 (2)
C15	0.0221 (19)	0.035 (2)	0.037 (2)	0.0014 (18)	0.0067 (17)	0.004 (2)
C16	0.024 (2)	0.059 (3)	0.043 (3)	0.000 (2)	0.0042 (19)	−0.012 (2)
C17	0.030 (2)	0.063 (3)	0.037 (2)	0.003 (2)	0.0095 (19)	−0.009 (2)
C18	0.027 (2)	0.047 (3)	0.034 (2)	−0.0030 (19)	0.0032 (18)	−0.002 (2)
C19	0.030 (2)	0.041 (3)	0.036 (2)	0.0031 (19)	0.0113 (18)	−0.002 (2)
C20	0.024 (2)	0.034 (2)	0.033 (2)	0.0018 (17)	0.0050 (17)	0.0063 (19)
C21	0.030 (2)	0.045 (3)	0.031 (2)	0.0014 (19)	0.0024 (17)	0.004 (2)
C22	0.028 (2)	0.046 (3)	0.034 (2)	0.0023 (19)	0.0073 (18)	−0.004 (2)
C23	0.149 (6)	0.063 (4)	0.038 (3)	0.002 (4)	−0.002 (3)	−0.007 (3)
C24	0.156 (6)	0.038 (3)	0.040 (3)	0.006 (3)	0.000 (3)	−0.002 (3)
C25	0.040 (2)	0.037 (3)	0.037 (2)	0.0005 (19)	−0.0012 (19)	−0.006 (2)
C26	0.142 (6)	0.040 (3)	0.047 (3)	0.010 (3)	−0.006 (3)	−0.009 (3)
C27	0.132 (6)	0.048 (4)	0.063 (4)	0.013 (4)	−0.007 (4)	0.015 (3)

Zn1—O8	2.104 (3)	C6—C7	1.412 (7)
Zn1—O7	2.138 (3)	C7—C8	1.393 (7)
Zn1—N4	2.142 (3)	C7—C12	1.418 (7)
Zn1—N2	2.163 (4)	C8—C9	1.344 (8)
Zn1—N3i	2.175 (3)	C8—H8	0.9300
Zn1—N1	2.176 (3)	C9—C10	1.387 (7)
N1—C1	1.317 (5)	C9—H9	0.9300
N1—C5	1.362 (6)	C10—H10	0.9300
N2—C10	1.316 (5)	C11—C12	1.335 (8)
N2—C6	1.354 (5)	C11—H11	0.9300
N3—C13	1.328 (5)	C12—H12	0.9300
N3—C17	1.329 (5)	C13—C14	1.375 (5)
N4—C18	1.329 (5)	C13—H13	0.9300
N4—C22	1.338 (5)	C14—C15	1.378 (6)
N5—C27	1.295 (7)	C14—H14	0.9300
N5—C23	1.296 (7)	C15—C16	1.383 (5)
N6—O3	1.194 (6)	C15—C20	1.490 (5)
N6—O2	1.227 (5)	C16—C17	1.369 (5)
N6—O1	1.230 (5)	C16—H16	0.9300
N7—O4	1.167 (6)	C17—H17	0.9300
N7—O6	1.229 (6)	C18—C19	1.373 (5)
N7—O5	1.278 (8)	C18—H18	0.9300
O7—H7C	0.8500	C19—C20	1.389 (5)
O7—H7D	0.8500	C19—H19	0.9300
O8—H8C	0.8500	C20—C21	1.388 (5)
O8—H8D	0.8500	C21—C22	1.363 (5)
O9—H9C	0.8500	C21—H21	0.9300
O9—H9D	0.8500	C22—H22	0.9300
C1—C2	1.401 (7)	C23—C24	1.373 (7)
C1—H1	0.9300	C23—H23	0.9300
C2—C3	1.352 (8)	C24—C25	1.357 (6)
C2—H2	0.9300	C24—H24	0.9300
C3—C4	1.381 (8)	C25—C26	1.361 (7)
C3—H3	0.9300	C25—C25ii	1.492 (8)
C4—C5	1.403 (6)	C26—C27	1.370 (7)
C4—C11	1.434 (8)	C26—H26	0.9300
C5—C6	1.427 (6)	C27—H27	0.9300
O8—Zn1—O7	91.55 (12)	C6—C7—C12	118.8 (5)
O8—Zn1—N4	92.31 (11)	C9—C8—C7	119.8 (5)
O7—Zn1—N4	88.58 (12)	C9—C8—H8	120.1
O8—Zn1—N2	93.64 (13)	C7—C8—H8	120.1
O7—Zn1—N2	174.80 (12)	C8—C9—C10	119.8 (5)
N4—Zn1—N2	90.88 (12)	C8—C9—H9	120.1
O8—Zn1—N3i	85.28 (11)	C10—C9—H9	120.1
O7—Zn1—N3i	86.98 (12)	N2—C10—C9	122.9 (5)
N4—Zn1—N3i	174.89 (13)	N2—C10—H10	118.5
N2—Zn1—N3i	93.77 (13)	C9—C10—H10	118.5
O8—Zn1—N1	168.97 (13)	C12—C11—C4	121.9 (5)
O7—Zn1—N1	97.62 (13)	C12—C11—H11	119.0
N4—Zn1—N1	94.05 (12)	C4—C11—H11	119.0
N2—Zn1—N1	77.27 (14)	C11—C12—C7	121.2 (6)
N3i—Zn1—N1	89.06 (12)	C11—C12—H12	119.4
C1—N1—C5	118.6 (4)	C7—C12—H12	119.4
C1—N1—Zn1	128.6 (3)	N3—C13—C14	123.8 (4)
C5—N1—Zn1	112.6 (3)	N3—C13—H13	118.1
C10—N2—C6	118.2 (4)	C14—C13—H13	118.1
C10—N2—Zn1	128.1 (3)	C13—C14—C15	119.9 (4)
C6—N2—Zn1	113.7 (3)	C13—C14—H14	120.0
C13—N3—C17	116.3 (3)	C15—C14—H14	120.0
C13—N3—Zn1iii	121.3 (3)	C14—C15—C16	116.1 (4)
C17—N3—Zn1iii	122.3 (3)	C14—C15—C20	122.4 (4)
C18—N4—C22	116.5 (3)	C16—C15—C20	121.5 (4)
C18—N4—Zn1	122.0 (3)	C17—C16—C15	120.3 (4)
C22—N4—Zn1	121.4 (3)	C17—C16—H16	119.9
C27—N5—C23	114.8 (5)	C15—C16—H16	119.9
O3—N6—O2	122.4 (5)	N3—C17—C16	123.5 (4)
O3—N6—O1	120.1 (5)	N3—C17—H17	118.2
O2—N6—O1	117.5 (5)	C16—C17—H17	118.2
O4—N7—O6	124.0 (7)	N4—C18—C19	124.2 (4)
O4—N7—O5	118.0 (7)	N4—C18—H18	117.9
O6—N7—O5	118.0 (7)	C19—C18—H18	117.9
Zn1—O7—H7C	108.6	C18—C19—C20	119.1 (4)
Zn1—O7—H7D	115.9	C18—C19—H19	120.4
H7C—O7—H7D	108.4	C20—C19—H19	120.4
Zn1—O8—H8C	135.8	C21—C20—C19	116.6 (3)
Zn1—O8—H8D	109.0	C21—C20—C15	121.7 (3)
H8C—O8—H8D	108.1	C19—C20—C15	121.7 (3)
H9C—O9—H9D	108.3	C22—C21—C20	120.3 (4)
N1—C1—C2	121.9 (5)	C22—C21—H21	119.9
N1—C1—H1	119.1	C20—C21—H21	119.9
C2—C1—H1	119.1	N4—C22—C21	123.3 (4)
C3—C2—C1	119.8 (5)	N4—C22—H22	118.3
C3—C2—H2	120.1	C21—C22—H22	118.3
C1—C2—H2	120.1	N5—C23—C24	124.8 (5)
C2—C3—C4	120.0 (5)	N5—C23—H23	117.6
C2—C3—H3	120.0	C24—C23—H23	117.6
C4—C3—H3	120.0	C25—C24—C23	120.2 (5)
C3—C4—C5	117.7 (6)	C25—C24—H24	119.9
C3—C4—C11	123.7 (6)	C23—C24—H24	119.9
C5—C4—C11	118.5 (5)	C24—C25—C26	115.1 (4)
N1—C5—C4	122.0 (5)	C24—C25—C25ii	121.9 (5)
N1—C5—C6	118.5 (4)	C26—C25—C25ii	122.9 (5)
C4—C5—C6	119.5 (5)	C25—C26—C27	120.1 (5)
N2—C6—C7	122.1 (4)	C25—C26—H26	120.0
N2—C6—C5	117.8 (4)	C27—C26—H26	120.0
C7—C6—C5	120.1 (5)	N5—C27—C26	125.0 (6)
C8—C7—C6	117.2 (5)	N5—C27—H27	117.5
C8—C7—C12	124.0 (6)	C26—C27—H27	117.5
O8—Zn1—N1—C1	143.1 (6)	N2—C6—C7—C8	−1.6 (7)
O7—Zn1—N1—C1	−2.8 (4)	C5—C6—C7—C8	178.1 (4)
N4—Zn1—N1—C1	−91.9 (4)	N2—C6—C7—C12	179.0 (4)
N2—Zn1—N1—C1	178.1 (4)	C5—C6—C7—C12	−1.3 (7)
N3i—Zn1—N1—C1	84.0 (4)	C6—C7—C8—C9	0.4 (8)
O8—Zn1—N1—C5	−32.9 (8)	C12—C7—C8—C9	179.7 (6)
O7—Zn1—N1—C5	−178.8 (3)	C7—C8—C9—C10	1.2 (10)
N4—Zn1—N1—C5	92.1 (3)	C6—N2—C10—C9	0.7 (7)
N2—Zn1—N1—C5	2.1 (3)	Zn1—N2—C10—C9	−177.4 (4)
N3i—Zn1—N1—C5	−92.0 (3)	C8—C9—C10—N2	−1.9 (9)
O8—Zn1—N2—C10	−9.1 (4)	C3—C4—C11—C12	178.9 (6)
N4—Zn1—N2—C10	83.2 (4)	C5—C4—C11—C12	−0.7 (9)
N3i—Zn1—N2—C10	−94.6 (4)	C4—C11—C12—C7	1.7 (10)
N1—Zn1—N2—C10	177.2 (4)	C8—C7—C12—C11	−180.0 (6)
O8—Zn1—N2—C6	172.7 (3)	C6—C7—C12—C11	−0.7 (9)
N4—Zn1—N2—C6	−94.9 (3)	C17—N3—C13—C14	−0.9 (7)
N3i—Zn1—N2—C6	87.2 (3)	Zn1iii—N3—C13—C14	175.9 (4)
N1—Zn1—N2—C6	−1.0 (3)	N3—C13—C14—C15	−0.4 (7)
O8—Zn1—N4—C18	−142.9 (3)	C13—C14—C15—C16	1.0 (7)
O7—Zn1—N4—C18	−51.4 (3)	C13—C14—C15—C20	179.8 (4)
N2—Zn1—N4—C18	123.4 (3)	C14—C15—C16—C17	−0.3 (7)
N1—Zn1—N4—C18	46.1 (3)	C20—C15—C16—C17	−179.2 (4)
O8—Zn1—N4—C22	41.6 (3)	C13—N3—C17—C16	1.6 (7)
O7—Zn1—N4—C22	133.1 (3)	Zn1iii—N3—C17—C16	−175.1 (4)
N2—Zn1—N4—C22	−52.0 (3)	C15—C16—C17—N3	−1.0 (7)
N1—Zn1—N4—C22	−129.3 (3)	C22—N4—C18—C19	2.1 (6)
C5—N1—C1—C2	−0.1 (7)	Zn1—N4—C18—C19	−173.6 (3)
Zn1—N1—C1—C2	−175.8 (4)	N4—C18—C19—C20	0.3 (7)
N1—C1—C2—C3	−0.5 (8)	C18—C19—C20—C21	−2.1 (6)
C1—C2—C3—C4	0.2 (9)	C18—C19—C20—C15	176.6 (4)
C2—C3—C4—C5	0.7 (8)	C14—C15—C20—C21	9.3 (6)
C2—C3—C4—C11	−179.0 (6)	C16—C15—C20—C21	−171.9 (4)
C1—N1—C5—C4	1.0 (6)	C14—C15—C20—C19	−169.3 (4)
Zn1—N1—C5—C4	177.4 (3)	C16—C15—C20—C19	9.5 (6)
C1—N1—C5—C6	−179.4 (4)	C19—C20—C21—C22	1.6 (6)
Zn1—N1—C5—C6	−3.0 (5)	C15—C20—C21—C22	−177.1 (4)
C3—C4—C5—N1	−1.3 (7)	C18—N4—C22—C21	−2.6 (6)
C11—C4—C5—N1	178.4 (4)	Zn1—N4—C22—C21	173.1 (3)
C3—C4—C5—C6	179.1 (4)	C20—C21—C22—N4	0.8 (6)
C11—C4—C5—C6	−1.2 (7)	C27—N5—C23—C24	−0.5 (10)
C10—N2—C6—C7	1.1 (6)	N5—C23—C24—C25	−0.2 (11)
Zn1—N2—C6—C7	179.4 (3)	C23—C24—C25—C26	1.1 (9)
C10—N2—C6—C5	−178.6 (4)	C23—C24—C25—C25ii	−178.4 (6)
Zn1—N2—C6—C5	−0.3 (4)	C24—C25—C26—C27	−1.3 (9)
N1—C5—C6—N2	2.3 (6)	C25ii—C25—C26—C27	178.1 (6)
C4—C5—C6—N2	−178.1 (4)	C23—N5—C27—C26	0.2 (10)
N1—C5—C6—C7	−177.4 (4)	C25—C26—C27—N5	0.8 (11)
C4—C5—C6—C7	2.2 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7C···O1iv	0.85	1.89	2.737 (5)	180
O7—H7D···O6v	0.85	1.93	2.782 (5)	180
O8—H8C···N5	0.85	1.89	2.724 (5)	169
O8—H8D···O3iv	0.85	1.90	2.744 (6)	169
O9—H9C···O2iii	0.85	2.24	3.091 (7)	176
O9—H9D···O4vi	0.85	2.27	3.114 (8)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7C⋯O1i	0.85	1.89	2.737 (5)	180
O7—H7D⋯O6ii	0.85	1.93	2.782 (5)	180
O8—H8C⋯N5	0.85	1.89	2.724 (5)	169
O8—H8D⋯O3i	0.85	1.90	2.744 (6)	169
O9—H9C⋯O2iii	0.85	2.24	3.091 (7)	176
O9—H9D⋯O4iv	0.85	2.27	3.114 (8)	176

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