Poly[[μ(2)-1,3-bis-(imidazol-1-ylmeth-yl)benzene][μ(2)-2,2'-dihy-droxy-1,1'-methyl-enebis(naphthalene-3-carboxyl-ato)]zinc].

In the title compound, [Zn(C(23)H(14)O(6))(C(14)H(14)N(4))](n), the Zn(II) ion is four-coordinated in a distorted tetra-hedral geometry. The 1,3-bis-(imidazol-1-ylmeth-yl)benzene and 2,2'-dihy-droxy-1,1'-methyl-enebis(naphthalene-3-carboxy-l-ate) ligands con-nect the Zn(II) ions alternately in different directions, forming a layered structure parallel to the ac plane. Topological analysis reveals that the whole structure is a (4,4) network. The layers are further assembled into a three-dimensional supra-molecular structure via C-H⋯O and C-H⋯π inter-actions.

Related literature

For background to metal-organic frameworks, see: Luo et al. (2009 ▶); Wei et al. (2010 ▶). For related structures, see: Wang et al. (2011 ▶); Fan et al. (2005 ▶); Zhou et al. (2008 ▶); Li et al. (2010 ▶); Feng et al. (2009 ▶); Xu et al. (2009 ▶); Batten & Robson (1998 ▶).

Experimental

Crystal data

[Zn(C23H14O6)(C14H14N4)]

M = 690.00

Monoclinic,

a = 10.8382 (9) Å

b = 17.3428 (16) Å

c = 17.7939 (17) Å

β = 100.781 (1)°

V = 3285.6 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.80 mm−1

T = 298 K

0.23 × 0.17 × 0.15 mm

Data collection

Bruker SMART-1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.837, T max = 0.889

16511 measured reflections

5800 independent reflections

2460 reflections with I > 2σ(I)

R int = 0.111

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.127

S = 1.00

5800 reflections

433 parameters

H-atom parameters constrained

Δρmax = 0.67 e Å−3

Δρmin = −0.68 e Å−3

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

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811054584/vm2140sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811054584/vm2140Isup2.hkl

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

[Zn(C23H14O6)(C14H14N4)]	F(000) = 1424
Mr = 690.00	Dx = 1.395 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1774 reflections
a = 10.8382 (9) Å	θ = 2.3–26.1°
b = 17.3428 (16) Å	µ = 0.80 mm−1
c = 17.7939 (17) Å	T = 298 K
β = 100.781 (1)°	Block, colorless
V = 3285.6 (5) Å3	0.23 × 0.17 × 0.15 mm
Z = 4

Bruker SMART-1000 CCD diffractometer	5800 independent reflections
Radiation source: fine-focus sealed tube	2460 reflections with I > 2σ(I)
graphite	Rint = 0.111
phi and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→12
Tmin = 0.837, Tmax = 0.889	k = −20→18
16511 measured reflections	l = −21→19

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: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0236P)2] where P = (Fo2 + 2Fc2)/3
5800 reflections	(Δ/σ)max = 0.001
433 parameters	Δρmax = 0.67 e Å−3
0 restraints	Δρmin = −0.67 e Å−3

	x	y	z	Uiso*/Ueq
Zn1	−0.39449 (6)	0.50406 (4)	0.24221 (4)	0.0467 (2)
O1	−0.3107 (4)	0.5943 (2)	0.2949 (2)	0.0604 (12)
O2	−0.1690 (4)	0.5185 (2)	0.3671 (2)	0.0699 (12)
O3	−0.0023 (4)	0.57744 (19)	0.4719 (2)	0.0619 (12)
H3	−0.0409	0.5448	0.4434	0.093*
O4	0.5308 (4)	0.9456 (2)	0.6440 (2)	0.0611 (12)
O5	0.3738 (4)	0.9219 (2)	0.7034 (2)	0.0763 (14)
O6	0.2189 (4)	0.8163 (2)	0.6615 (2)	0.0700 (13)
H6	0.2553	0.8513	0.6876	0.105*
N1	−0.1407 (4)	0.3384 (3)	0.1945 (3)	0.0495 (13)
N2	−0.2782 (4)	0.4302 (3)	0.2033 (3)	0.0495 (13)
N3	0.3730 (5)	0.4304 (3)	0.3875 (3)	0.0554 (13)
N4	0.5190 (5)	0.4570 (3)	0.3194 (3)	0.0532 (13)
C1	−0.2182 (6)	0.5840 (4)	0.3479 (3)	0.0505 (16)
C2	0.4305 (7)	0.9104 (3)	0.6495 (4)	0.0503 (16)
C3	0.1095 (5)	0.7031 (3)	0.5576 (3)	0.0495 (15)
H3A	0.1300	0.6487	0.5626	0.059*
H3B	0.0865	0.7195	0.6052	0.059*
C4	−0.0044 (6)	0.7121 (3)	0.4946 (3)	0.0386 (12)
C5	−0.0545 (5)	0.6475 (3)	0.4542 (3)	0.0446 (15)
C6	−0.1615 (5)	0.6530 (3)	0.3926 (3)	0.0424 (14)
C7	−0.2144 (5)	0.7256 (3)	0.3752 (3)	0.0503 (16)
H7	−0.2815	0.7305	0.3344	0.060*
C8	−0.1694 (6)	0.7915 (3)	0.4174 (3)	0.0525 (16)
C9	−0.0664 (5)	0.7846 (3)	0.4788 (3)	0.0445 (15)
C10	−0.0301 (6)	0.8524 (3)	0.5231 (3)	0.0536 (17)
H10	0.0375	0.8493	0.5638	0.064*
C11	−0.0892 (7)	0.9204 (4)	0.5084 (4)	0.070 (2)
H11	−0.0649	0.9625	0.5402	0.084*
C12	−0.1880 (8)	0.9278 (4)	0.4450 (5)	0.080 (2)
H12	−0.2263	0.9755	0.4338	0.096*
C13	−0.2281 (6)	0.8654 (4)	0.3996 (4)	0.0688 (19)
H13	−0.2929	0.8708	0.3576	0.083*
C14	0.2276 (5)	0.7466 (3)	0.5483 (3)	0.0448 (15)
C15	0.2754 (6)	0.8037 (3)	0.5997 (3)	0.0468 (15)
C16	0.3828 (5)	0.8488 (3)	0.5920 (3)	0.0443 (15)
C17	0.4395 (5)	0.8354 (3)	0.5311 (3)	0.0511 (16)
H17	0.5063	0.8666	0.5241	0.061*
C18	0.3996 (5)	0.7754 (3)	0.4782 (3)	0.0486 (15)
C19	0.2920 (5)	0.7298 (3)	0.4877 (3)	0.0431 (14)
C20	0.2585 (6)	0.6664 (3)	0.4362 (3)	0.0530 (16)
H20	0.1903	0.6353	0.4407	0.064*
C21	0.3278 (6)	0.6513 (3)	0.3798 (3)	0.0605 (18)
H21	0.3052	0.6097	0.3472	0.073*
C22	0.4289 (7)	0.6959 (4)	0.3705 (4)	0.074 (2)
H22	0.4727	0.6849	0.3316	0.088*
C23	0.4644 (6)	0.7565 (4)	0.4189 (4)	0.0646 (18)
H23	0.5332	0.7862	0.4125	0.077*
C24	−0.2301 (6)	0.3633 (3)	0.2317 (3)	0.0512 (16)
H24	−0.2551	0.3372	0.2720	0.061*
C25	−0.2178 (7)	0.4463 (4)	0.1459 (4)	0.082 (2)
H25	−0.2320	0.4898	0.1150	0.098*
C26	−0.1329 (7)	0.3902 (4)	0.1392 (4)	0.081 (2)
H26	−0.0802	0.3880	0.1036	0.098*
C27	0.3969 (6)	0.4536 (3)	0.3211 (3)	0.0494 (15)
H27	0.3345	0.4664	0.2796	0.059*
C28	0.5744 (6)	0.4335 (4)	0.3922 (4)	0.071 (2)
H28	0.6606	0.4293	0.4096	0.085*
C29	0.4875 (7)	0.4179 (4)	0.4341 (4)	0.079 (2)
H29	0.5015	0.4017	0.4848	0.095*
C30	−0.0691 (6)	0.2657 (3)	0.2106 (3)	0.0576 (17)
H30A	−0.0437	0.2486	0.1639	0.069*
H30B	−0.1246	0.2267	0.2249	0.069*
C31	0.2486 (6)	0.4144 (3)	0.4057 (3)	0.0644 (18)
H31A	0.1919	0.4568	0.3884	0.077*
H31B	0.2554	0.4094	0.4607	0.077*
C32	0.0448 (6)	0.2705 (3)	0.2720 (3)	0.0489 (16)
C33	0.0892 (6)	0.3386 (3)	0.3090 (3)	0.0545 (16)
H33	0.0464	0.3845	0.2953	0.065*
C34	0.1966 (6)	0.3394 (4)	0.3661 (4)	0.0567 (17)
C35	0.2594 (6)	0.2702 (4)	0.3865 (4)	0.0680 (19)
H35	0.3304	0.2691	0.4250	0.082*
C36	0.2149 (7)	0.2026 (4)	0.3485 (4)	0.070 (2)
H36	0.2580	0.1566	0.3610	0.084*
C37	0.1091 (6)	0.2030 (4)	0.2934 (4)	0.0598 (18)
H37	0.0797	0.1569	0.2699	0.072*

	U11	U22	U33	U12	U13	U23
Zn1	0.0379 (4)	0.0440 (4)	0.0570 (4)	0.0013 (4)	0.0059 (3)	0.0023 (4)
O1	0.053 (3)	0.063 (3)	0.060 (3)	−0.009 (2)	−0.002 (2)	0.000 (2)
O2	0.064 (3)	0.047 (3)	0.089 (3)	−0.008 (2)	−0.012 (2)	−0.006 (2)
O3	0.056 (3)	0.029 (2)	0.091 (3)	−0.004 (2)	−0.012 (2)	0.001 (2)
O4	0.057 (3)	0.054 (3)	0.068 (3)	−0.011 (2)	0.001 (2)	−0.001 (2)
O5	0.086 (4)	0.079 (3)	0.064 (3)	−0.025 (3)	0.014 (3)	−0.026 (3)
O6	0.075 (3)	0.084 (3)	0.055 (3)	−0.031 (3)	0.022 (3)	−0.019 (2)
N1	0.041 (3)	0.049 (3)	0.060 (3)	0.011 (3)	0.013 (3)	0.004 (3)
N2	0.045 (3)	0.051 (3)	0.053 (3)	0.009 (3)	0.010 (3)	0.008 (3)
N3	0.044 (4)	0.062 (3)	0.062 (4)	−0.005 (3)	0.013 (3)	0.003 (3)
N4	0.048 (4)	0.059 (3)	0.053 (3)	0.010 (3)	0.008 (3)	0.004 (3)
C1	0.048 (5)	0.048 (4)	0.057 (4)	−0.011 (4)	0.011 (3)	−0.002 (3)
C2	0.050 (5)	0.049 (4)	0.049 (4)	−0.002 (4)	0.003 (4)	0.002 (3)
C3	0.049 (4)	0.055 (4)	0.043 (4)	−0.004 (3)	0.003 (3)	−0.001 (3)
C4	0.034 (3)	0.042 (3)	0.041 (3)	−0.007 (3)	0.011 (3)	−0.005 (3)
C5	0.036 (4)	0.049 (4)	0.049 (4)	−0.007 (3)	0.009 (3)	0.007 (3)
C6	0.036 (4)	0.045 (3)	0.049 (4)	−0.007 (3)	0.016 (3)	0.005 (3)
C7	0.032 (4)	0.064 (4)	0.056 (4)	−0.007 (3)	0.009 (3)	0.006 (3)
C8	0.045 (4)	0.046 (4)	0.072 (5)	−0.006 (3)	0.024 (4)	−0.001 (3)
C9	0.032 (4)	0.044 (4)	0.060 (4)	−0.010 (3)	0.018 (3)	0.000 (3)
C10	0.048 (4)	0.053 (4)	0.063 (4)	−0.008 (4)	0.018 (3)	−0.009 (3)
C11	0.077 (6)	0.042 (4)	0.096 (6)	−0.012 (4)	0.031 (5)	−0.012 (4)
C12	0.077 (6)	0.039 (4)	0.129 (7)	0.005 (4)	0.036 (5)	−0.002 (4)
C13	0.052 (5)	0.060 (4)	0.096 (5)	0.011 (4)	0.018 (4)	0.019 (4)
C14	0.041 (4)	0.049 (4)	0.046 (4)	−0.005 (3)	0.013 (3)	−0.001 (3)
C15	0.048 (4)	0.053 (4)	0.040 (4)	−0.012 (3)	0.012 (3)	−0.004 (3)
C16	0.043 (4)	0.043 (3)	0.044 (4)	−0.001 (3)	0.000 (3)	−0.002 (3)
C17	0.037 (4)	0.052 (4)	0.061 (4)	−0.008 (3)	0.003 (3)	0.004 (3)
C18	0.039 (4)	0.055 (4)	0.050 (4)	−0.001 (3)	0.006 (3)	−0.010 (3)
C19	0.033 (4)	0.042 (3)	0.052 (4)	0.001 (3)	0.001 (3)	−0.002 (3)
C20	0.051 (4)	0.051 (4)	0.054 (4)	0.003 (3)	0.000 (3)	−0.009 (3)
C21	0.054 (5)	0.065 (4)	0.059 (4)	0.000 (4)	0.003 (4)	−0.018 (4)
C22	0.059 (5)	0.100 (6)	0.065 (5)	0.000 (5)	0.021 (4)	−0.014 (4)
C23	0.052 (5)	0.074 (5)	0.070 (5)	−0.006 (4)	0.015 (4)	−0.005 (4)
C24	0.045 (4)	0.054 (4)	0.057 (4)	0.004 (3)	0.016 (3)	0.007 (3)
C25	0.104 (7)	0.070 (5)	0.083 (5)	0.026 (5)	0.047 (5)	0.028 (4)
C26	0.091 (6)	0.082 (5)	0.086 (5)	0.027 (5)	0.056 (5)	0.023 (4)
C27	0.043 (4)	0.056 (4)	0.049 (4)	−0.002 (3)	0.006 (3)	0.010 (3)
C28	0.033 (4)	0.091 (5)	0.088 (5)	−0.007 (4)	0.010 (4)	0.027 (4)
C29	0.060 (5)	0.105 (6)	0.066 (5)	−0.004 (5)	−0.005 (4)	0.025 (4)
C30	0.054 (5)	0.049 (4)	0.071 (4)	0.010 (3)	0.014 (4)	−0.003 (3)
C31	0.048 (5)	0.070 (5)	0.077 (5)	0.003 (4)	0.015 (4)	0.006 (4)
C32	0.042 (4)	0.052 (4)	0.054 (4)	0.006 (3)	0.014 (3)	0.005 (3)
C33	0.040 (4)	0.048 (4)	0.079 (5)	0.003 (3)	0.019 (4)	0.002 (4)
C34	0.049 (5)	0.055 (4)	0.071 (5)	−0.001 (4)	0.025 (4)	0.001 (4)
C35	0.055 (5)	0.074 (5)	0.073 (5)	0.005 (4)	0.009 (4)	0.018 (4)
C36	0.061 (5)	0.051 (4)	0.101 (6)	0.016 (4)	0.021 (5)	0.016 (4)
C37	0.058 (5)	0.051 (4)	0.072 (5)	0.005 (4)	0.018 (4)	0.006 (4)

Zn1—O1	1.957 (4)	C12—C13	1.371 (8)
Zn1—N4i	1.979 (5)	C12—H12	0.9300
Zn1—O4ii	1.985 (4)	C13—H13	0.9300
Zn1—N2	2.009 (5)	C14—C15	1.382 (7)
O1—C1	1.255 (7)	C14—C19	1.418 (7)
O2—C1	1.274 (6)	C15—C16	1.430 (7)
O3—C5	1.352 (6)	C16—C17	1.362 (7)
O3—H3	0.8200	C17—C18	1.415 (7)
O4—C2	1.267 (6)	C17—H17	0.9300
O4—Zn1iii	1.985 (4)	C18—C23	1.412 (7)
O5—C2	1.248 (6)	C18—C19	1.445 (7)
O6—C15	1.372 (5)	C19—C20	1.435 (7)
O6—H6	0.8200	C20—C21	1.386 (7)
N1—C24	1.342 (6)	C20—H20	0.9300
N1—C26	1.346 (6)	C21—C22	1.376 (8)
N1—C30	1.480 (6)	C21—H21	0.9300
N2—C24	1.332 (6)	C22—C23	1.368 (8)
N2—C25	1.342 (6)	C22—H22	0.9300
N3—C27	1.318 (6)	C23—H23	0.9300
N3—C29	1.374 (7)	C24—H24	0.9300
N3—C31	1.471 (7)	C25—C26	1.359 (8)
N4—C27	1.331 (6)	C25—H25	0.9300
N4—C28	1.383 (7)	C26—H26	0.9300
N4—Zn1iv	1.979 (5)	C27—H27	0.9300
C1—C6	1.503 (7)	C28—C29	1.335 (8)
C2—C16	1.502 (7)	C28—H28	0.9300
C3—C4	1.512 (7)	C29—H29	0.9300
C3—C14	1.521 (7)	C30—C32	1.490 (7)
C3—H3A	0.9700	C30—H30A	0.9700
C3—H3B	0.9700	C30—H30B	0.9700
C4—C5	1.387 (7)	C31—C34	1.535 (8)
C4—C9	1.429 (7)	C31—H31A	0.9700
C5—C6	1.442 (7)	C31—H31B	0.9700
C6—C7	1.393 (7)	C32—C37	1.379 (7)
C7—C8	1.405 (7)	C32—C33	1.394 (7)
C7—H7	0.9300	C33—C34	1.395 (8)
C8—C9	1.414 (7)	C33—H33	0.9300
C8—C13	1.440 (7)	C34—C35	1.395 (8)
C9—C10	1.428 (7)	C35—C36	1.393 (8)
C10—C11	1.344 (8)	C35—H35	0.9300
C10—H10	0.9300	C36—C37	1.362 (8)
C11—C12	1.409 (9)	C36—H36	0.9300
C11—H11	0.9300	C37—H37	0.9300
O1—Zn1—N4i	103.57 (17)	C17—C16—C2	120.9 (6)
O1—Zn1—O4ii	98.40 (16)	C15—C16—C2	120.4 (5)
N4i—Zn1—O4ii	128.6 (2)	C16—C17—C18	121.8 (5)
O1—Zn1—N2	114.19 (19)	C16—C17—H17	119.1
N4i—Zn1—N2	112.68 (19)	C18—C17—H17	119.1
O4ii—Zn1—N2	99.00 (18)	C23—C18—C17	122.3 (6)
C1—O1—Zn1	118.7 (4)	C23—C18—C19	119.1 (5)
C5—O3—H3	109.5	C17—C18—C19	118.5 (5)
C2—O4—Zn1iii	111.1 (4)	C14—C19—C20	122.7 (5)
C15—O6—H6	109.5	C14—C19—C18	119.9 (5)
C24—N1—C26	107.2 (5)	C20—C19—C18	117.3 (5)
C24—N1—C30	125.3 (5)	C21—C20—C19	120.0 (6)
C26—N1—C30	127.4 (5)	C21—C20—H20	120.0
C24—N2—C25	104.9 (5)	C19—C20—H20	120.0
C24—N2—Zn1	130.7 (4)	C22—C21—C20	122.2 (6)
C25—N2—Zn1	123.8 (4)	C22—C21—H21	118.9
C27—N3—C29	106.4 (5)	C20—C21—H21	118.9
C27—N3—C31	126.6 (6)	C23—C22—C21	119.5 (6)
C29—N3—C31	126.7 (6)	C23—C22—H22	120.2
C27—N4—C28	103.0 (5)	C21—C22—H22	120.2
C27—N4—Zn1iv	129.5 (4)	C22—C23—C18	121.9 (6)
C28—N4—Zn1iv	126.3 (4)	C22—C23—H23	119.1
O1—C1—O2	124.3 (6)	C18—C23—H23	119.1
O1—C1—C6	118.3 (6)	N2—C24—N1	111.1 (5)
O2—C1—C6	117.3 (6)	N2—C24—H24	124.4
O5—C2—O4	122.3 (6)	N1—C24—H24	124.4
O5—C2—C16	118.8 (6)	N2—C25—C26	110.6 (6)
O4—C2—C16	118.8 (6)	N2—C25—H25	124.7
C4—C3—C14	117.1 (4)	C26—C25—H25	124.7
C4—C3—H3A	108.0	N1—C26—C25	106.1 (5)
C14—C3—H3A	108.0	N1—C26—H26	127.0
C4—C3—H3B	108.0	C25—C26—H26	127.0
C14—C3—H3B	108.0	N3—C27—N4	113.3 (5)
H3A—C3—H3B	107.3	N3—C27—H27	123.3
C5—C4—C9	119.0 (6)	N4—C27—H27	123.3
C5—C4—C3	119.2 (5)	C29—C28—N4	110.8 (6)
C9—C4—C3	121.7 (5)	C29—C28—H28	124.6
O3—C5—C4	119.9 (5)	N4—C28—H28	124.6
O3—C5—C6	118.6 (5)	C28—C29—N3	106.4 (6)
C4—C5—C6	121.4 (5)	C28—C29—H29	126.8
C7—C6—C5	117.9 (5)	N3—C29—H29	126.8
C7—C6—C1	119.4 (5)	N1—C30—C32	115.3 (5)
C5—C6—C1	122.7 (5)	N1—C30—H30A	108.4
C6—C7—C8	121.9 (6)	C32—C30—H30A	108.4
C6—C7—H7	119.0	N1—C30—H30B	108.4
C8—C7—H7	119.0	C32—C30—H30B	108.4
C7—C8—C9	119.3 (5)	H30A—C30—H30B	107.5
C7—C8—C13	120.8 (6)	N3—C31—C34	109.3 (5)
C9—C8—C13	119.9 (6)	N3—C31—H31A	109.8
C8—C9—C10	116.9 (5)	C34—C31—H31A	109.8
C8—C9—C4	120.1 (5)	N3—C31—H31B	109.8
C10—C9—C4	123.0 (6)	C34—C31—H31B	109.8
C11—C10—C9	122.9 (6)	H31A—C31—H31B	108.3
C11—C10—H10	118.6	C37—C32—C33	118.5 (6)
C9—C10—H10	118.6	C37—C32—C30	117.5 (6)
C10—C11—C12	119.9 (6)	C33—C32—C30	124.0 (6)
C10—C11—H11	120.0	C32—C33—C34	121.3 (6)
C12—C11—H11	120.0	C32—C33—H33	119.3
C13—C12—C11	120.6 (7)	C34—C33—H33	119.3
C13—C12—H12	119.7	C35—C34—C33	118.7 (6)
C11—C12—H12	119.7	C35—C34—C31	119.4 (6)
C12—C13—C8	119.7 (7)	C33—C34—C31	121.8 (6)
C12—C13—H13	120.2	C36—C35—C34	119.4 (6)
C8—C13—H13	120.2	C36—C35—H35	120.3
C15—C14—C19	118.3 (5)	C34—C35—H35	120.3
C15—C14—C3	120.1 (5)	C37—C36—C35	120.9 (6)
C19—C14—C3	121.6 (5)	C37—C36—H36	119.5
O6—C15—C14	118.5 (5)	C35—C36—H36	119.5
O6—C15—C16	118.9 (5)	C36—C37—C32	121.1 (6)
C14—C15—C16	122.6 (5)	C36—C37—H37	119.5
C17—C16—C15	118.7 (5)	C32—C37—H37	119.5
N4i—Zn1—O1—C1	71.0 (5)	O5—C2—C16—C15	−0.8 (8)
O4ii—Zn1—O1—C1	−155.8 (4)	O4—C2—C16—C15	175.1 (5)
N2—Zn1—O1—C1	−51.9 (5)	C15—C16—C17—C18	−3.8 (8)
O1—Zn1—N2—C24	101.2 (5)	C2—C16—C17—C18	177.1 (5)
N4i—Zn1—N2—C24	−16.6 (6)	C16—C17—C18—C23	−174.2 (5)
O4ii—Zn1—N2—C24	−155.3 (5)	C16—C17—C18—C19	3.0 (8)
O1—Zn1—N2—C25	−68.4 (5)	C15—C14—C19—C20	173.1 (5)
N4i—Zn1—N2—C25	173.8 (5)	C3—C14—C19—C20	−6.5 (8)
O4ii—Zn1—N2—C25	35.1 (5)	C15—C14—C19—C18	−4.0 (8)
Zn1—O1—C1—O2	4.7 (8)	C3—C14—C19—C18	176.4 (5)
Zn1—O1—C1—C6	−174.7 (3)	C23—C18—C19—C14	178.3 (5)
Zn1iii—O4—C2—O5	15.3 (7)	C17—C18—C19—C14	1.0 (8)
Zn1iii—O4—C2—C16	−160.4 (4)	C23—C18—C19—C20	1.1 (8)
C14—C3—C4—C5	119.1 (6)	C17—C18—C19—C20	−176.2 (5)
C14—C3—C4—C9	−64.8 (7)	C14—C19—C20—C21	−177.7 (5)
C9—C4—C5—O3	−175.4 (5)	C18—C19—C20—C21	−0.6 (8)
C3—C4—C5—O3	0.8 (8)	C19—C20—C21—C22	−0.5 (9)
C9—C4—C5—C6	5.0 (8)	C20—C21—C22—C23	1.1 (10)
C3—C4—C5—C6	−178.8 (5)	C21—C22—C23—C18	−0.5 (10)
O3—C5—C6—C7	179.8 (5)	C17—C18—C23—C22	176.6 (6)
C4—C5—C6—C7	−0.6 (8)	C19—C18—C23—C22	−0.6 (9)
O3—C5—C6—C1	0.6 (8)	C25—N2—C24—N1	1.1 (7)
C4—C5—C6—C1	−179.8 (5)	Zn1—N2—C24—N1	−170.0 (4)
O1—C1—C6—C7	1.3 (8)	C26—N1—C24—N2	−1.4 (7)
O2—C1—C6—C7	−178.1 (5)	C30—N1—C24—N2	−179.2 (5)
O1—C1—C6—C5	−179.5 (5)	C24—N2—C25—C26	−0.3 (8)
O2—C1—C6—C5	1.1 (8)	Zn1—N2—C25—C26	171.5 (5)
C5—C6—C7—C8	−2.4 (8)	C24—N1—C26—C25	1.1 (8)
C1—C6—C7—C8	176.8 (5)	C30—N1—C26—C25	178.9 (6)
C6—C7—C8—C9	0.8 (8)	N2—C25—C26—N1	−0.5 (9)
C6—C7—C8—C13	−178.1 (5)	C29—N3—C27—N4	0.6 (7)
C7—C8—C9—C10	−175.8 (5)	C31—N3—C27—N4	−174.6 (5)
C13—C8—C9—C10	3.1 (8)	C28—N4—C27—N3	−0.1 (7)
C7—C8—C9—C4	3.8 (8)	Zn1iv—N4—C27—N3	−168.4 (4)
C13—C8—C9—C4	−177.3 (5)	C27—N4—C28—C29	−0.5 (7)
C5—C4—C9—C8	−6.6 (8)	Zn1iv—N4—C28—C29	168.4 (4)
C3—C4—C9—C8	177.3 (5)	N4—C28—C29—N3	0.8 (8)
C5—C4—C9—C10	172.9 (5)	C27—N3—C29—C28	−0.8 (7)
C3—C4—C9—C10	−3.2 (8)	C31—N3—C29—C28	174.3 (6)
C8—C9—C10—C11	0.1 (8)	C24—N1—C30—C32	−86.1 (7)
C4—C9—C10—C11	−179.5 (5)	C26—N1—C30—C32	96.6 (7)
C9—C10—C11—C12	−3.0 (9)	C27—N3—C31—C34	72.1 (7)
C10—C11—C12—C13	2.7 (10)	C29—N3—C31—C34	−102.1 (7)
C11—C12—C13—C8	0.5 (10)	N1—C30—C32—C37	174.9 (5)
C7—C8—C13—C12	175.5 (6)	N1—C30—C32—C33	−4.6 (8)
C9—C8—C13—C12	−3.4 (9)	C37—C32—C33—C34	0.4 (8)
C4—C3—C14—C15	116.3 (6)	C30—C32—C33—C34	180.0 (5)
C4—C3—C14—C19	−64.1 (7)	C32—C33—C34—C35	−0.5 (9)
C19—C14—C15—O6	−175.4 (5)	C32—C33—C34—C31	178.2 (5)
C3—C14—C15—O6	4.2 (8)	N3—C31—C34—C35	63.5 (7)
C19—C14—C15—C16	3.2 (9)	N3—C31—C34—C33	−115.1 (6)
C3—C14—C15—C16	−177.2 (5)	C33—C34—C35—C36	1.1 (9)
O6—C15—C16—C17	179.3 (5)	C31—C34—C35—C36	−177.6 (5)
C14—C15—C16—C17	0.6 (9)	C34—C35—C36—C37	−1.8 (10)
O6—C15—C16—C2	−1.6 (8)	C35—C36—C37—C32	1.8 (10)
C14—C15—C16—C2	179.7 (5)	C33—C32—C37—C36	−1.1 (9)
O5—C2—C16—C17	178.3 (5)	C30—C32—C37—C36	179.3 (5)
O4—C2—C16—C17	−5.8 (8)

Cg1, Cg2 and Cg3 are the centroids of the C8–C13, C18–C23 and C4–C9 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.82	1.81	2.555 (5)	150
O6—H6···O5	0.82	1.76	2.502 (5)	150
C30—H30B···O6v	0.97	2.54	3.350 (7)	141
C26—H26···Cg1vi	0.93	2.79	3.676 (8)	161
C29—H29···Cg2vii	0.93	2.76	3.502 (7)	137
C30—H30A···Cg3vi	0.97	2.71	3.628 (6)	158

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C8–C13, C18–C23 and C4–C9 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2	0.82	1.81	2.555 (5)	150
O6—H6⋯O5	0.82	1.76	2.502 (5)	150
C30—H30B⋯O6i	0.97	2.54	3.350 (7)	141
C26—H26⋯Cg1ii	0.93	2.79	3.676 (8)	161
C29—H29⋯Cg2iii	0.93	2.76	3.502 (7)	137
C30—H30A⋯Cg3ii	0.97	2.71	3.628 (6)	158

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