catena-Poly[[[aqua­zinc(II)]-μ-6-[bis­(2-pyridylmethyl)amino]caproato] perchlorate]

The tetra­dentate Schiff base carboxyl­ate-containing ligand bis­(2-pyridylmeth­yl)amino-6-caproic acid (Hpmca) reacts with zinc(II) perchlorate to give the title one-dimensional zinc(II) complex, {[Zn(C₁₈H₂₂N₃O₂)(H₂O)](ClO₄)}_n or {[Zn(μ-pmca)(H₂O)](ClO₄)}_n. Each Zn^II ion has a distorted octa­hedral geometry, being coordinated by three N atoms of the ligand, two O atoms belonging to another ligand, and one water mol­ecule.

Key indicators

• Single-crystal X-ray study
• T = 234 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.041
• wR factor = 0.127
• Data-to-parameter ratio = 18.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl1
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SMART (Bruker, 1999); data reduction: SAINT-Plus (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

catena-Poly[[Aqua[bis(2-pyridylmethyl)amino-6-caproato]zinc(II) perchlorate]

Crystal data

[Zn(C18H22N3O2)(H2O)](ClO4)	F(000) = 2048
Mr = 495.22	Dx = 1.603 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4492 reflections
a = 15.9996 (7) Å	θ = 2.6–23.1°
b = 15.3187 (6) Å	µ = 1.37 mm^−1
c = 16.7417 (7) Å	T = 234 K
V = 4103.3 (3) Å^3	Block, colourless
Z = 8	0.31 × 0.18 × 0.13 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	5109 independent reflections
Radiation source: fine-focus sealed tube	3087 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
ω scans	θmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan SADABS (Sheldrick, 1996)	h = −21→19
Tmin = 0.646, Tmax = 0.840	k = −20→12
28748 measured reflections	l = −21→22

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0446P)^2 + 6.9671P] where P = (Fo^2 + 2Fc^2)/3
5109 reflections	(Δ/σ)max < 0.001
277 parameters	Δρmax = 0.55 e Å^−3
0 restraints	Δρmin = −0.39 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Zn	0.01668 (3)	0.45775 (2)	0.35349 (2)	0.03238 (12)
Cl1	−0.30246 (7)	0.40472 (7)	0.53505 (6)	0.0536 (3)
O1	−0.01237 (16)	0.38347 (15)	0.45502 (13)	0.0379 (6)
O2	−0.04708 (17)	0.32496 (17)	0.34124 (13)	0.0429 (6)
O3	−0.3419 (3)	0.4593 (3)	0.4783 (3)	0.1016 (13)
O4	−0.2452 (3)	0.3500 (3)	0.4968 (2)	0.1002 (13)
O5	−0.3653 (2)	0.3565 (3)	0.5763 (3)	0.0928 (12)
O6	−0.2593 (2)	0.4582 (3)	0.5897 (2)	0.1038 (15)
OW1	0.0840 (2)	0.55871 (19)	0.41010 (17)	0.0461 (7)
H19A	0.064 (3)	0.578 (3)	0.446 (3)	0.055*
H19B	0.134 (3)	0.557 (3)	0.415 (3)	0.055*
N1	−0.08408 (19)	0.54498 (19)	0.35616 (17)	0.0380 (7)
N2	0.0318 (2)	0.52091 (19)	0.23721 (16)	0.0385 (7)
N3	0.13118 (19)	0.40398 (19)	0.32071 (17)	0.0374 (7)
C1	−0.1456 (3)	0.5483 (3)	0.4094 (2)	0.0475 (9)
H1	−0.1519	0.5016	0.4445	0.057*
C2	−0.2006 (3)	0.6171 (3)	0.4155 (3)	0.0551 (11)
H2	−0.2428	0.6171	0.4537	0.066*
C3	−0.1913 (3)	0.6857 (3)	0.3634 (3)	0.0642 (13)
H3	−0.2275	0.7332	0.3658	0.077*
C4	−0.1288 (3)	0.6838 (3)	0.3083 (3)	0.0608 (12)
H4	−0.1223	0.7296	0.2724	0.073*
C5	−0.0750 (3)	0.6135 (2)	0.3060 (2)	0.0450 (9)
C6	0.0011 (3)	0.6123 (2)	0.2525 (2)	0.0488 (10)
H6A	−0.0127	0.6397	0.2019	0.059*
H6B	0.0454	0.6461	0.2772	0.059*
C7	0.1227 (3)	0.5186 (3)	0.2205 (2)	0.0490 (10)
H7A	0.1482	0.5712	0.2415	0.059*
H7B	0.1312	0.5182	0.1632	0.059*
C8	0.1660 (2)	0.4402 (2)	0.2563 (2)	0.0435 (9)
C9	0.2415 (3)	0.4090 (3)	0.2266 (3)	0.0580 (11)
H9	0.2640	0.4323	0.1800	0.070*
C10	0.2822 (3)	0.3442 (3)	0.2663 (3)	0.0609 (12)
H10	0.3336	0.3243	0.2479	0.073*
C11	0.2466 (3)	0.3076 (3)	0.3345 (3)	0.0556 (11)
H11	0.2731	0.2631	0.3625	0.067*
C12	0.1708 (2)	0.3402 (3)	0.3585 (2)	0.0448 (9)
H12	0.1459	0.3162	0.4037	0.054*
C13	−0.0419 (2)	0.3197 (2)	0.41514 (19)	0.0338 (7)
C14	−0.0688 (2)	0.2380 (2)	0.45814 (19)	0.0367 (8)
H14A	−0.0576	0.1884	0.4237	0.044*
H14B	−0.1287	0.2406	0.4665	0.044*
C15	−0.0269 (2)	0.2217 (2)	0.5383 (2)	0.0395 (8)
H15A	0.0330	0.2293	0.5327	0.047*
H15B	−0.0468	0.2643	0.5767	0.047*
C16	−0.0450 (2)	0.1305 (2)	0.5692 (2)	0.0387 (8)
H16A	−0.0293	0.0885	0.5286	0.046*
H16B	−0.1046	0.1248	0.5782	0.046*
C17	0.0011 (2)	0.1083 (2)	0.6466 (2)	0.0397 (8)
H17A	0.0608	0.1158	0.6391	0.048*
H17B	−0.0168	0.1474	0.6889	0.048*
C18	−0.0175 (3)	0.4852 (2)	0.1699 (2)	0.0416 (9)
H18A	−0.0082	0.5220	0.1235	0.050*
H18B	−0.0763	0.4894	0.1835	0.050*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn	0.0405 (2)	0.0313 (2)	0.02534 (19)	−0.00151 (17)	0.00170 (17)	0.00090 (16)
Cl1	0.0480 (6)	0.0581 (6)	0.0545 (6)	−0.0027 (5)	−0.0035 (5)	−0.0098 (5)
O1	0.0503 (15)	0.0352 (13)	0.0283 (11)	−0.0044 (11)	0.0022 (11)	−0.0010 (10)
O2	0.0538 (16)	0.0472 (15)	0.0278 (12)	−0.0059 (12)	−0.0051 (11)	0.0057 (11)
O3	0.106 (3)	0.106 (3)	0.092 (3)	0.018 (3)	−0.014 (2)	0.030 (2)
O4	0.090 (3)	0.106 (3)	0.104 (3)	0.024 (2)	0.011 (2)	−0.042 (3)
O5	0.083 (3)	0.082 (3)	0.113 (3)	−0.015 (2)	0.017 (2)	0.016 (2)
O6	0.065 (2)	0.145 (4)	0.102 (3)	−0.013 (2)	−0.011 (2)	−0.066 (3)
OW1	0.0466 (17)	0.0514 (17)	0.0402 (15)	−0.0049 (14)	−0.0009 (13)	−0.0151 (12)
N1	0.0422 (17)	0.0382 (15)	0.0336 (14)	0.0021 (13)	−0.0019 (13)	−0.0001 (13)
N2	0.054 (2)	0.0344 (16)	0.0270 (14)	−0.0072 (13)	0.0024 (13)	−0.0024 (12)
N3	0.0424 (18)	0.0392 (16)	0.0305 (14)	−0.0038 (13)	0.0020 (13)	−0.0046 (13)
C1	0.057 (3)	0.046 (2)	0.040 (2)	0.0032 (19)	−0.0030 (18)	0.0036 (17)
C2	0.055 (3)	0.059 (3)	0.052 (2)	0.013 (2)	−0.002 (2)	−0.002 (2)
C3	0.079 (3)	0.050 (3)	0.063 (3)	0.024 (2)	0.005 (3)	0.004 (2)
C4	0.081 (4)	0.040 (2)	0.061 (3)	0.012 (2)	−0.003 (2)	0.008 (2)
C5	0.065 (3)	0.038 (2)	0.0321 (19)	−0.0008 (18)	−0.0058 (17)	−0.0008 (16)
C6	0.075 (3)	0.038 (2)	0.0339 (18)	−0.0050 (19)	0.0011 (18)	0.0018 (16)
C7	0.063 (3)	0.051 (2)	0.0337 (19)	−0.016 (2)	0.0054 (18)	0.0006 (17)
C8	0.046 (2)	0.049 (2)	0.0350 (18)	−0.0136 (17)	0.0050 (16)	−0.0101 (17)
C9	0.054 (3)	0.071 (3)	0.049 (2)	−0.012 (2)	0.018 (2)	−0.007 (2)
C10	0.039 (2)	0.076 (3)	0.067 (3)	−0.004 (2)	0.009 (2)	−0.021 (2)
C11	0.042 (2)	0.061 (3)	0.064 (3)	0.003 (2)	−0.001 (2)	−0.007 (2)
C12	0.045 (2)	0.049 (2)	0.040 (2)	−0.0027 (18)	0.0032 (17)	−0.0058 (18)
C13	0.0323 (18)	0.041 (2)	0.0286 (16)	0.0036 (15)	0.0022 (14)	0.0032 (15)
C14	0.043 (2)	0.0371 (19)	0.0302 (17)	−0.0023 (16)	−0.0026 (15)	0.0044 (14)
C15	0.053 (2)	0.0364 (19)	0.0293 (17)	0.0008 (17)	−0.0013 (16)	0.0033 (14)
C16	0.047 (2)	0.0382 (19)	0.0306 (17)	0.0021 (16)	0.0017 (16)	0.0015 (15)
C17	0.056 (2)	0.0366 (19)	0.0268 (16)	0.0021 (16)	0.0010 (16)	−0.0009 (14)
C18	0.062 (3)	0.0361 (18)	0.0264 (16)	−0.0039 (18)	−0.0039 (17)	−0.0013 (14)

Geometric parameters (Å, º)

Zn—N3	2.082 (3)	C5—C6	1.512 (6)
Zn—N1	2.094 (3)	C6—H6A	0.9700
Zn—O1	2.098 (2)	C6—H6B	0.9700
Zn—OW1	2.110 (3)	C7—C8	1.511 (6)
Zn—N2	2.187 (3)	C7—H7A	0.9700
Zn—O2	2.285 (3)	C7—H7B	0.9700
Zn—C13	2.533 (3)	C8—C9	1.391 (6)
Cl1—O4	1.397 (4)	C9—C10	1.360 (6)
Cl1—O6	1.409 (3)	C9—H9	0.9300
Cl1—O3	1.414 (4)	C10—C11	1.393 (6)
Cl1—O5	1.425 (4)	C10—H10	0.9300
O1—C13	1.274 (4)	C11—C12	1.372 (6)
O2—C13	1.242 (4)	C11—H11	0.9300
OW1—H19A	0.74 (4)	C12—H12	0.9300
OW1—H19B	0.80 (5)	C13—C14	1.507 (5)
N1—C1	1.329 (5)	C14—C15	1.519 (5)
N1—C5	1.352 (5)	C14—H14A	0.9700
N2—C18	1.481 (4)	C14—H14B	0.9700
N2—C7	1.481 (5)	C15—C16	1.518 (5)
N2—C6	1.506 (5)	C15—H15A	0.9700
N3—C12	1.326 (5)	C15—H15B	0.9700
N3—C8	1.334 (4)	C16—C17	1.530 (5)
C1—C2	1.377 (6)	C16—H16A	0.9700
C1—H1	0.9300	C16—H16B	0.9700
C2—C3	1.374 (6)	C17—C18^i	1.515 (5)
C2—H2	0.9300	C17—H17A	0.9700
C3—C4	1.362 (6)	C17—H17B	0.9700
C3—H3	0.9300	C18—C17^ii	1.515 (5)
C4—C5	1.378 (6)	C18—H18A	0.9700
C4—H4	0.9300	C18—H18B	0.9700
N3—Zn—N1	159.26 (12)	C5—C6—H6A	109.2
N3—Zn—O1	101.18 (11)	N2—C6—H6B	109.2
N1—Zn—O1	99.10 (11)	C5—C6—H6B	109.2
N3—Zn—OW1	87.66 (12)	H6A—C6—H6B	107.9
N1—Zn—OW1	85.17 (12)	N2—C7—C8	113.2 (3)
O1—Zn—OW1	98.44 (10)	N2—C7—H7A	108.9
N3—Zn—N2	80.98 (12)	C8—C7—H7A	108.9
N1—Zn—N2	79.74 (11)	N2—C7—H7B	108.9
O1—Zn—N2	170.28 (10)	C8—C7—H7B	108.9
OW1—Zn—N2	91.09 (11)	H7A—C7—H7B	107.7
N3—Zn—O2	90.97 (11)	N3—C8—C9	120.6 (4)
N1—Zn—O2	103.08 (11)	N3—C8—C7	117.4 (3)
O1—Zn—O2	59.39 (8)	C9—C8—C7	121.9 (4)
OW1—Zn—O2	157.07 (10)	C10—C9—C8	119.4 (4)
N2—Zn—O2	111.30 (9)	C10—C9—H9	120.3
N3—Zn—C13	95.90 (11)	C8—C9—H9	120.3
N1—Zn—C13	103.83 (11)	C9—C10—C11	119.9 (4)
O1—Zn—C13	30.11 (10)	C9—C10—H10	120.1
OW1—Zn—C13	128.17 (11)	C11—C10—H10	120.1
N2—Zn—C13	140.61 (11)	C12—C11—C10	117.1 (4)
O2—Zn—C13	29.31 (9)	C12—C11—H11	121.5
O4—Cl1—O6	109.0 (3)	C10—C11—H11	121.5
O4—Cl1—O3	109.8 (3)	N3—C12—C11	123.4 (4)
O6—Cl1—O3	108.1 (3)	N3—C12—H12	118.3
O4—Cl1—O5	112.0 (3)	C11—C12—H12	118.3
O6—Cl1—O5	109.4 (3)	O2—C13—O1	119.8 (3)
O3—Cl1—O5	108.5 (3)	O2—C13—C14	120.7 (3)
C13—O1—Zn	94.21 (19)	O1—C13—C14	119.5 (3)
C13—O2—Zn	86.5 (2)	O2—C13—Zn	64.20 (19)
Zn—OW1—H19A	116 (4)	O1—C13—Zn	55.67 (16)
Zn—OW1—H19B	122 (3)	C14—C13—Zn	173.6 (2)
H19A—OW1—H19B	111 (5)	C13—C14—C15	115.6 (3)
C1—N1—C5	117.8 (3)	C13—C14—H14A	108.4
C1—N1—Zn	127.5 (3)	C15—C14—H14A	108.4
C5—N1—Zn	113.6 (3)	C13—C14—H14B	108.4
C18—N2—C7	111.7 (3)	C15—C14—H14B	108.4
C18—N2—C6	107.4 (3)	H14A—C14—H14B	107.4
C7—N2—C6	112.0 (3)	C16—C15—C14	111.6 (3)
C18—N2—Zn	117.1 (2)	C16—C15—H15A	109.3
C7—N2—Zn	105.4 (2)	C14—C15—H15A	109.3
C6—N2—Zn	103.0 (2)	C16—C15—H15B	109.3
C12—N3—C8	119.5 (3)	C14—C15—H15B	109.3
C12—N3—Zn	125.9 (2)	H15A—C15—H15B	108.0
C8—N3—Zn	114.6 (3)	C15—C16—C17	113.7 (3)
N1—C1—C2	123.5 (4)	C15—C16—H16A	108.8
N1—C1—H1	118.3	C17—C16—H16A	108.8
C2—C1—H1	118.3	C15—C16—H16B	108.8
C3—C2—C1	118.1 (4)	C17—C16—H16B	108.8
C3—C2—H2	121.0	H16A—C16—H16B	107.7
C1—C2—H2	121.0	C18^i—C17—C16	109.4 (3)
C4—C3—C2	119.5 (4)	C18^i—C17—H17A	109.8
C4—C3—H3	120.2	C16—C17—H17A	109.8
C2—C3—H3	120.2	C18^i—C17—H17B	109.8
C3—C4—C5	119.6 (4)	C16—C17—H17B	109.8
C3—C4—H4	120.2	H17A—C17—H17B	108.2
C5—C4—H4	120.2	N2—C18—C17^ii	116.1 (3)
N1—C5—C4	121.5 (4)	N2—C18—H18A	108.3
N1—C5—C6	116.4 (3)	C17^ii—C18—H18A	108.3
C4—C5—C6	121.9 (4)	N2—C18—H18B	108.3
N2—C6—C5	112.0 (3)	C17^ii—C18—H18B	108.3
N2—C6—H6A	109.2	H18A—C18—H18B	107.4
N3—Zn—O1—C13	−82.4 (2)	C1—C2—C3—C4	−0.2 (7)
N1—Zn—O1—C13	101.9 (2)	C2—C3—C4—C5	−0.7 (7)
OW1—Zn—O1—C13	−171.7 (2)	C1—N1—C5—C4	−1.6 (6)
O2—Zn—O1—C13	2.02 (19)	Zn—N1—C5—C4	−170.3 (3)
N3—Zn—O2—C13	100.4 (2)	C1—N1—C5—C6	173.5 (3)
N1—Zn—O2—C13	−95.0 (2)	Zn—N1—C5—C6	4.8 (4)
O1—Zn—O2—C13	−2.1 (2)	C3—C4—C5—N1	1.6 (7)
OW1—Zn—O2—C13	14.1 (4)	C3—C4—C5—C6	−173.2 (4)
N2—Zn—O2—C13	−178.9 (2)	C18—N2—C6—C5	84.5 (4)
N3—Zn—N1—C1	−167.5 (3)	C7—N2—C6—C5	−152.4 (3)
O1—Zn—N1—C1	0.5 (3)	Zn—N2—C6—C5	−39.6 (3)
OW1—Zn—N1—C1	−97.3 (3)	N1—C5—C6—N2	25.6 (5)
N2—Zn—N1—C1	170.7 (3)	C4—C5—C6—N2	−159.3 (4)
O2—Zn—N1—C1	61.0 (3)	C18—N2—C7—C8	−97.2 (4)
C13—Zn—N1—C1	30.9 (3)	C6—N2—C7—C8	142.3 (3)
N3—Zn—N1—C5	−0.1 (5)	Zn—N2—C7—C8	31.0 (3)
O1—Zn—N1—C5	167.8 (2)	C12—N3—C8—C9	2.8 (5)
OW1—Zn—N1—C5	70.0 (2)	Zn—N3—C8—C9	−178.3 (3)
N2—Zn—N1—C5	−21.9 (2)	C12—N3—C8—C7	−173.9 (3)
O2—Zn—N1—C5	−131.6 (2)	Zn—N3—C8—C7	5.0 (4)
C13—Zn—N1—C5	−161.8 (2)	N2—C7—C8—N3	−26.0 (5)
N3—Zn—N2—C18	102.7 (3)	N2—C7—C8—C9	157.4 (3)
N1—Zn—N2—C18	−85.0 (3)	N3—C8—C9—C10	−3.6 (6)
OW1—Zn—N2—C18	−169.8 (3)	C7—C8—C9—C10	173.0 (4)
O2—Zn—N2—C18	15.2 (3)	C8—C9—C10—C11	2.2 (7)
C13—Zn—N2—C18	14.4 (4)	C9—C10—C11—C12	−0.2 (6)
N3—Zn—N2—C7	−22.2 (2)	C8—N3—C12—C11	−0.8 (6)
N1—Zn—N2—C7	150.1 (2)	Zn—N3—C12—C11	−179.5 (3)
OW1—Zn—N2—C7	65.2 (2)	C10—C11—C12—N3	−0.5 (6)
O2—Zn—N2—C7	−109.7 (2)	Zn—O2—C13—O1	3.4 (3)
C13—Zn—N2—C7	−110.6 (2)	Zn—O2—C13—C14	−175.4 (3)
N3—Zn—N2—C6	−139.8 (2)	Zn—O1—C13—O2	−3.7 (4)
N1—Zn—N2—C6	32.6 (2)	Zn—O1—C13—C14	175.1 (3)
OW1—Zn—N2—C6	−52.3 (2)	N3—Zn—C13—O2	−81.4 (2)
O2—Zn—N2—C6	132.7 (2)	N1—Zn—C13—O2	92.2 (2)
C13—Zn—N2—C6	131.9 (2)	O1—Zn—C13—O2	176.5 (3)
N1—Zn—N3—C12	167.3 (3)	OW1—Zn—C13—O2	−173.1 (2)
O1—Zn—N3—C12	−0.6 (3)	N2—Zn—C13—O2	1.6 (3)
OW1—Zn—N3—C12	97.5 (3)	N3—Zn—C13—O1	102.1 (2)
N2—Zn—N3—C12	−171.0 (3)	N1—Zn—C13—O1	−84.3 (2)
O2—Zn—N3—C12	−59.6 (3)	OW1—Zn—C13—O1	10.5 (3)
C13—Zn—N3—C12	−30.6 (3)	N2—Zn—C13—O1	−174.9 (2)
N1—Zn—N3—C8	−11.5 (5)	O2—Zn—C13—O1	−176.5 (3)
O1—Zn—N3—C8	−179.4 (2)	O2—C13—C14—C15	154.2 (3)
OW1—Zn—N3—C8	−81.3 (3)	O1—C13—C14—C15	−24.6 (5)
N2—Zn—N3—C8	10.2 (2)	C13—C14—C15—C16	−169.0 (3)
O2—Zn—N3—C8	121.6 (2)	C14—C15—C16—C17	175.6 (3)
C13—Zn—N3—C8	150.6 (2)	C15—C16—C17—C18^i	−177.0 (3)
C5—N1—C1—C2	0.6 (6)	C7—N2—C18—C17^ii	59.2 (4)
Zn—N1—C1—C2	167.5 (3)	C6—N2—C18—C17^ii	−177.6 (3)
N1—C1—C2—C3	0.2 (7)	Zn—N2—C18—C17^ii	−62.5 (4)

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
OW1—H19A···O1^iii	0.74 (4)	1.95 (5)	2.683 (4)	175 (5)
OW1—H19B···O6^iii	0.80 (5)	2.02 (5)	2.817 (5)	171 (4)

Symmetry code: (iii) −x, −y+1, −z+1.