Hydro­thermal synthesis, crystal structure and photoluminescence of two homochiral zinc(II) coordination polymers

Metal-organic frameworks (MOFs) have potentially useful applications and an intriguing variety of architectures and topologies. Two homochiral coordination polymers have been synthesized by the hydro­thermal method, namely poly[([mu]-N-benzyl-L-phenyl­alaninato-[kappa]⁴O,O':O,N)([mu]-formato-[kappa]²O:O')zinc(II)], [Zn(C₁₆H₁₆NO₂)(HCOO)]_n, (1), and poly[([mu]-N-benzyl-L-leucinato-[kappa]⁴O,O':O,N)([mu]-formato-[kappa]²O:O')zinc(II)], [Zn(C₁₃H₁₈NO₂)(HCOO)]_n, (2), and studied by single-crystal X-ray diffraction, elemental analyses, IR spectroscopy and fluorescence spectroscopy. Compounds (1) and (2) each have a two-dimensional layer structure, with the benzyl or isobutyl groups of the ligands directed towards the inter­layer inter­face. Photoluminescence investigations show that both (1) and (2) display a strong emission in the blue region.

Computing details

For both compounds, data collection: SMART (Bruker, 1999); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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: SHELXL97 (Sheldrick, 2008).

(1) Poly[(µ-N-benzyl-L-phenylalaninato-κ⁴O,O':O,N)(µ-formato-κ²O:O')zinc(II)],

Crystal data

[Zn(C16H16NO2)(HCO2)]	Z = 4
Mr = 364.69	F(000) = 752
Monoclinic, C2	Dx = 1.478 Mg m^−3
Hall symbol: C 2y	Mo Kα radiation, λ = 0.71073 Å
a = 33.2283 (19) Å	µ = 1.52 mm^−1
b = 6.6469 (4) Å	T = 293 K
c = 7.4241 (4) Å	Needle, white
β = 91.299 (5)°	0.26 × 0.05 × 0.04 mm
V = 1639.30 (16) Å^3

Data collection

Bruker APEX CCD area-detector diffractometer	2909 independent reflections
Radiation source: fine-focus sealed tube	2563 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
ω scans	θmax = 26.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −40→39
Tmin = 0.694, Tmax = 0.942	k = −8→7
5538 measured reflections	l = −8→9

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.078	w = 1/[σ^2(Fo^2) + (0.0264P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max = 0.001
2909 reflections	Δρmax = 0.52 e Å^−3
208 parameters	Δρmin = −0.36 e Å^−3
1 restraint	Absolute structure: Flack (1983), with 1154 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.009 (17)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Zn1	0.233914 (10)	0.42083 (8)	0.73454 (5)	0.03079 (13)
N1	0.17375 (8)	0.3623 (4)	0.6437 (4)	0.0304 (8)
H1B	0.1597	0.4709	0.6397	0.036*
O1	0.24190 (8)	0.1911 (5)	0.5410 (4)	0.0392 (7)
O2	0.21213 (8)	0.0329 (4)	0.3117 (4)	0.0392 (7)
O3	0.24662 (8)	0.2510 (4)	0.9489 (4)	0.0394 (7)
O4	0.29276 (8)	0.1716 (4)	1.1569 (4)	0.0463 (8)
C1	0.02920 (17)	0.1151 (12)	0.7521 (10)	0.093 (2)
H1A	0.0017	0.0893	0.7477	0.111*
C2	0.05512 (18)	−0.0259 (11)	0.8210 (10)	0.101 (3)
H2A	0.0452	−0.1462	0.8659	0.121*
C3	0.09645 (16)	0.0098 (9)	0.8246 (8)	0.0717 (17)
H3A	0.1141	−0.0879	0.8690	0.086*
C4	0.11124 (12)	0.1906 (8)	0.7620 (6)	0.0442 (11)
C5	0.08440 (13)	0.3284 (8)	0.6956 (7)	0.0614 (15)
H5A	0.0939	0.4506	0.6526	0.074*
C6	0.04331 (15)	0.2908 (10)	0.6905 (8)	0.0793 (19)
H6A	0.0256	0.3872	0.6446	0.095*
C7	0.15600 (12)	0.2295 (8)	0.7796 (6)	0.0481 (12)
H7A	0.1615	0.2874	0.8976	0.058*
H7B	0.1698	0.1010	0.7757	0.058*
C8	0.17382 (11)	0.2780 (6)	0.4625 (5)	0.0281 (9)
H8A	0.1506	0.1887	0.4462	0.034*
C9	0.21230 (12)	0.1574 (6)	0.4396 (6)	0.0330 (9)
C10	0.17216 (10)	0.4422 (9)	0.3178 (5)	0.0368 (10)
H10A	0.1913	0.5469	0.3500	0.044*
H10B	0.1801	0.3849	0.2039	0.044*
C11	0.13122 (12)	0.5339 (6)	0.2949 (6)	0.0385 (10)
C12	0.12273 (16)	0.7232 (8)	0.3638 (8)	0.0676 (16)
H12A	0.1432	0.7977	0.4193	0.081*
C13	0.08452 (18)	0.8022 (9)	0.3512 (10)	0.090 (2)
H13A	0.0794	0.9293	0.3976	0.108*
C14	0.05434 (18)	0.6950 (11)	0.2711 (10)	0.093 (2)
H14A	0.0284	0.7478	0.2656	0.111*
C15	0.06178 (16)	0.5078 (10)	0.1977 (8)	0.081 (2)
H15A	0.0413	0.4352	0.1404	0.097*
C16	0.10044 (11)	0.4307 (12)	0.2113 (5)	0.0521 (11)
H16A	0.1057	0.3049	0.1622	0.063*
C17	0.27963 (12)	0.2741 (6)	1.0299 (6)	0.0390 (10)
H17A	0.2959	0.3785	0.9909	0.047*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0324 (2)	0.0312 (2)	0.0285 (2)	−0.0020 (3)	−0.00401 (15)	0.0016 (3)
N1	0.0302 (16)	0.031 (2)	0.0296 (18)	0.0029 (13)	0.0007 (13)	−0.0032 (13)
O1	0.0337 (17)	0.0432 (17)	0.040 (2)	0.0097 (14)	−0.0080 (14)	−0.0090 (15)
O2	0.0373 (16)	0.0433 (16)	0.0369 (18)	0.0064 (13)	−0.0001 (13)	−0.0157 (15)
O3	0.0460 (17)	0.0373 (16)	0.0344 (18)	−0.0074 (14)	−0.0087 (14)	0.0120 (13)
O4	0.0523 (18)	0.0430 (17)	0.043 (2)	−0.0019 (15)	−0.0129 (14)	0.0177 (15)
C1	0.051 (4)	0.122 (6)	0.106 (6)	−0.033 (4)	0.007 (3)	0.003 (5)
C2	0.069 (4)	0.104 (8)	0.130 (6)	−0.038 (4)	0.005 (4)	0.018 (5)
C3	0.056 (3)	0.070 (4)	0.090 (5)	−0.015 (3)	−0.003 (3)	0.009 (3)
C4	0.041 (2)	0.061 (3)	0.031 (3)	−0.010 (2)	0.0051 (19)	−0.003 (2)
C5	0.040 (3)	0.075 (4)	0.070 (4)	−0.008 (2)	0.007 (2)	0.005 (3)
C6	0.038 (3)	0.110 (5)	0.090 (5)	0.006 (3)	0.008 (3)	0.015 (4)
C7	0.041 (2)	0.072 (3)	0.031 (3)	−0.009 (2)	0.0029 (19)	0.002 (2)
C8	0.0262 (19)	0.030 (2)	0.028 (2)	−0.0040 (17)	−0.0010 (16)	−0.0018 (17)
C9	0.038 (2)	0.030 (2)	0.030 (2)	0.0020 (18)	0.0023 (18)	0.0036 (19)
C10	0.0328 (18)	0.047 (3)	0.031 (2)	−0.004 (3)	0.0006 (15)	0.006 (3)
C11	0.037 (2)	0.040 (2)	0.039 (3)	0.000 (2)	−0.0054 (19)	0.007 (2)
C12	0.064 (3)	0.040 (3)	0.098 (5)	0.006 (3)	−0.013 (3)	0.002 (3)
C13	0.083 (4)	0.055 (4)	0.132 (7)	0.026 (3)	0.000 (4)	−0.003 (4)
C14	0.056 (4)	0.088 (5)	0.133 (7)	0.033 (4)	−0.010 (4)	0.024 (5)
C15	0.047 (3)	0.113 (6)	0.082 (4)	−0.007 (3)	−0.021 (3)	0.012 (4)
C16	0.048 (2)	0.062 (3)	0.046 (2)	0.007 (4)	−0.0087 (18)	−0.004 (4)
C17	0.045 (2)	0.034 (2)	0.037 (3)	−0.010 (2)	−0.007 (2)	0.006 (2)

Geometric parameters (Å, º)

Zn1—O2^i	1.979 (3)	C5—C6	1.388 (6)
Zn1—O3	1.988 (3)	C5—H5A	0.9300
Zn1—O4^ii	2.061 (3)	C6—H6A	0.9300
Zn1—O1	2.118 (3)	C7—H7A	0.9700
Zn1—N1	2.131 (3)	C7—H7B	0.9700
N1—C8	1.457 (5)	C8—C9	1.522 (5)
N1—C7	1.474 (5)	C8—C10	1.531 (6)
N1—H1B	0.8600	C8—H8A	0.9800
O1—C9	1.245 (5)	C10—C11	1.497 (5)
O2—C9	1.259 (5)	C10—H10A	0.9700
O2—Zn1^iii	1.979 (3)	C10—H10B	0.9700
O3—C17	1.248 (4)	C11—C16	1.368 (6)
O4—C17	1.235 (5)	C11—C12	1.390 (6)
O4—Zn1^iv	2.061 (3)	C12—C13	1.375 (7)
C1—C6	1.343 (9)	C12—H12A	0.9300
C1—C2	1.364 (9)	C13—C14	1.356 (8)
C1—H1A	0.9300	C13—H13A	0.9300
C2—C3	1.393 (7)	C14—C15	1.383 (9)
C2—H2A	0.9300	C14—H14A	0.9300
C3—C4	1.383 (7)	C15—C16	1.385 (7)
C3—H3A	0.9300	C15—H15A	0.9300
C4—C5	1.363 (6)	C16—H16A	0.9300
C4—C7	1.512 (5)	C17—H17A	0.9300
O2^i—Zn1—O3	100.12 (11)	C4—C7—H7A	108.1
O2^i—Zn1—O4^ii	99.37 (13)	N1—C7—H7B	108.1
O3—Zn1—O4^ii	103.38 (12)	C4—C7—H7B	108.1
O2^i—Zn1—O1	91.49 (12)	H7A—C7—H7B	107.3
O3—Zn1—O1	96.08 (12)	N1—C8—C9	108.9 (3)
O4^ii—Zn1—O1	155.56 (11)	N1—C8—C10	111.9 (3)
O2^i—Zn1—N1	149.45 (12)	C9—C8—C10	108.3 (3)
O3—Zn1—N1	109.27 (12)	N1—C8—H8A	109.2
O4^ii—Zn1—N1	82.11 (11)	C9—C8—H8A	109.2
O1—Zn1—N1	77.57 (11)	C10—C8—H8A	109.2
C8—N1—C7	114.3 (3)	O1—C9—O2	124.3 (4)
C8—N1—Zn1	109.9 (2)	O1—C9—C8	119.5 (4)
C7—N1—Zn1	106.3 (2)	O2—C9—C8	116.2 (3)
C8—N1—H1B	107.6	C11—C10—C8	112.9 (3)
C7—N1—H1B	107.5	C11—C10—H10A	109.0
Zn1—N1—H1B	111.2	C8—C10—H10A	109.0
C9—O1—Zn1	115.5 (3)	C11—C10—H10B	109.0
C9—O2—Zn1^iii	112.9 (2)	C8—C10—H10B	109.0
C17—O3—Zn1	119.0 (3)	H10A—C10—H10B	107.8
C17—O4—Zn1^iv	126.7 (3)	C16—C11—C12	117.7 (5)
C6—C1—C2	120.2 (6)	C16—C11—C10	121.0 (4)
C6—C1—H1A	119.9	C12—C11—C10	121.2 (4)
C2—C1—H1A	119.9	C13—C12—C11	121.0 (5)
C1—C2—C3	120.2 (6)	C13—C12—H12A	119.5
C1—C2—H2A	119.9	C11—C12—H12A	119.5
C3—C2—H2A	119.9	C14—C13—C12	120.1 (6)
C4—C3—C2	120.0 (6)	C14—C13—H13A	120.0
C4—C3—H3A	120.0	C12—C13—H13A	120.0
C2—C3—H3A	120.0	C13—C14—C15	120.6 (5)
C5—C4—C3	118.1 (4)	C13—C14—H14A	119.7
C5—C4—C7	123.4 (4)	C15—C14—H14A	119.7
C3—C4—C7	118.4 (5)	C16—C15—C14	118.5 (6)
C4—C5—C6	121.6 (5)	C16—C15—H15A	120.7
C4—C5—H5A	119.2	C14—C15—H15A	120.7
C6—C5—H5A	119.2	C11—C16—C15	122.0 (6)
C1—C6—C5	119.9 (6)	C11—C16—H16A	119.0
C1—C6—H6A	120.1	C15—C16—H16A	119.0
C5—C6—H6A	120.1	O4—C17—O3	126.3 (4)
N1—C7—C4	116.8 (4)	O4—C17—H17A	116.9
N1—C7—H7A	108.1	O3—C17—H17A	116.9

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

(2) Poly[(µ-N-benzyl-L-leucinato-κ⁴O,O':O,N)(µ-formato-κ²O:O')zinc(II)],

Crystal data

[Zn(C13H18NO2)(HCO2)]	Z = 4
Mr = 330.67	F(000) = 688
Orthorhombic, P212121	Dx = 1.438 Mg m^−3
Hall symbol: P 2ac 2ab	Mo Kα radiation, λ = 0.71073 Å
a = 6.4790 (4) Å	µ = 1.62 mm^−1
b = 7.6577 (4) Å	T = 293 K
c = 30.7746 (19) Å	Needle, white
V = 1526.86 (16) Å^3	0.24 × 0.07 × 0.06 mm

Data collection

Bruker APEX CCD area-detector diffractometer	2886 independent reflections
Radiation source: fine-focus sealed tube	2661 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω scans	θmax = 26.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→7
Tmin = 0.697, Tmax = 0.909	k = −9→5
4702 measured reflections	l = −37→27

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.069	H-atom parameters constrained
wR(F^2) = 0.135	w = 1/[σ^2(Fo^2) + (0.0155P)^2 + 6.1609P] where P = (Fo^2 + 2Fc^2)/3
S = 1.17	(Δ/σ)max < 0.001
2886 reflections	Δρmax = 1.31 e Å^−3
181 parameters	Δρmin = −1.19 e Å^−3
0 restraints	Absolute structure: Flack (1983), with 1117 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (4)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Zn1	0.12573 (12)	0.48766 (10)	0.01666 (2)	0.0284 (2)
N1	0.1917 (9)	0.4143 (7)	0.08201 (18)	0.0297 (13)
H1B	0.0798	0.4189	0.0970	0.036*
O1	0.3434 (7)	0.2859 (7)	0.00767 (16)	0.0348 (12)
O3	−0.1279 (9)	0.6024 (7)	0.04675 (16)	0.0457 (13)
O2	0.4980 (7)	0.0621 (6)	0.04052 (16)	0.0351 (12)
O4	−0.1931 (7)	0.8106 (7)	−0.00242 (18)	0.0384 (14)
C4	0.3823 (13)	0.5194 (11)	0.1481 (2)	0.0431 (17)
C13	0.3805 (12)	0.1942 (9)	0.0403 (2)	0.0335 (16)
C7	0.3372 (12)	0.5431 (9)	0.1002 (2)	0.0390 (19)
H7A	0.2811	0.6592	0.0958	0.047*
H7B	0.4660	0.5359	0.0843	0.047*
C8	0.2726 (10)	0.2330 (9)	0.0829 (2)	0.0279 (15)
H8A	0.3722	0.2220	0.1067	0.033*
C14	−0.2239 (11)	0.7302 (9)	0.0325 (2)	0.0326 (17)
H14A	−0.3312	0.7714	0.0498	0.039*
C10	0.0087 (14)	0.0964 (11)	0.1362 (3)	0.045 (2)
H10A	−0.0376	0.2145	0.1437	0.054*
C9	0.0964 (12)	0.1030 (9)	0.0901 (2)	0.0338 (17)
H9A	0.1454	−0.0127	0.0825	0.041*
H9B	−0.0149	0.1319	0.0702	0.041*
C12	0.1687 (14)	0.0427 (15)	0.1695 (3)	0.070 (3)
H12A	0.1072	0.0415	0.1979	0.105*
H12B	0.2811	0.1244	0.1691	0.105*
H12C	0.2194	−0.0718	0.1626	0.105*
C11	−0.1795 (13)	−0.0228 (19)	0.1376 (3)	0.075 (3)
H11A	−0.2338	−0.0258	0.1666	0.112*
H11B	−0.1402	−0.1386	0.1290	0.112*
H11C	−0.2830	0.0208	0.1181	0.112*
C1	0.460 (2)	0.458 (2)	0.2350 (3)	0.088 (4)
H1A	0.4856	0.4343	0.2642	0.106*
C5	0.2290 (15)	0.5402 (13)	0.1788 (3)	0.059 (3)
H5A	0.0977	0.5741	0.1700	0.071*
C3	0.5749 (14)	0.4706 (14)	0.1623 (3)	0.064 (3)
H3A	0.6813	0.4586	0.1422	0.077*
C2	0.6137 (19)	0.4389 (17)	0.2055 (3)	0.087 (4)
H2A	0.7447	0.4047	0.2145	0.105*
C6	0.2675 (17)	0.512 (2)	0.2223 (3)	0.082 (3)
H6A	0.1638	0.5284	0.2428	0.098*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0329 (4)	0.0183 (3)	0.0340 (4)	−0.0008 (4)	−0.0026 (3)	0.0053 (4)
N1	0.031 (3)	0.027 (3)	0.031 (3)	0.000 (2)	0.004 (2)	0.000 (2)
O1	0.030 (3)	0.038 (3)	0.037 (3)	0.013 (2)	0.003 (2)	0.006 (2)
O3	0.045 (3)	0.041 (3)	0.051 (3)	0.025 (3)	0.001 (3)	0.018 (2)
O2	0.038 (3)	0.019 (3)	0.049 (3)	0.021 (2)	0.007 (2)	0.004 (2)
O4	0.032 (3)	0.031 (3)	0.052 (3)	0.008 (2)	0.003 (2)	0.007 (2)
C4	0.054 (4)	0.036 (4)	0.039 (4)	−0.006 (6)	−0.005 (4)	−0.008 (3)
C13	0.037 (4)	0.027 (4)	0.036 (4)	−0.018 (4)	−0.002 (4)	0.003 (3)
C7	0.049 (5)	0.024 (4)	0.044 (4)	−0.002 (4)	−0.002 (4)	−0.004 (3)
C8	0.030 (3)	0.019 (4)	0.034 (4)	0.010 (3)	−0.004 (3)	0.002 (3)
C14	0.029 (4)	0.024 (4)	0.044 (4)	0.002 (3)	0.000 (3)	0.004 (3)
C10	0.051 (5)	0.043 (5)	0.042 (4)	−0.001 (4)	0.012 (4)	0.006 (4)
C9	0.045 (4)	0.021 (3)	0.036 (4)	0.000 (3)	0.005 (4)	0.006 (3)
C12	0.075 (6)	0.089 (9)	0.045 (5)	−0.017 (6)	−0.005 (5)	0.025 (5)
C11	0.062 (6)	0.107 (10)	0.056 (5)	−0.030 (7)	0.008 (4)	0.013 (7)
C1	0.105 (9)	0.122 (13)	0.037 (5)	−0.010 (9)	−0.020 (6)	0.001 (6)
C5	0.069 (6)	0.057 (7)	0.051 (5)	0.009 (5)	−0.002 (4)	−0.014 (5)
C3	0.065 (6)	0.070 (7)	0.057 (5)	0.003 (6)	−0.008 (4)	−0.003 (5)
C2	0.071 (7)	0.125 (12)	0.066 (6)	0.013 (9)	−0.021 (6)	0.002 (6)
C6	0.093 (7)	0.111 (10)	0.040 (5)	0.002 (9)	0.014 (5)	−0.019 (8)

Geometric parameters (Å, º)

Zn1—O2^i	1.982 (5)	C14—H14A	0.9300
Zn1—O4^ii	1.989 (5)	C10—C12	1.514 (11)
Zn1—O3	2.081 (5)	C10—C11	1.524 (12)
Zn1—O1	2.110 (5)	C10—C9	1.531 (10)
Zn1—N1	2.132 (6)	C10—H10A	0.9800
N1—C7	1.475 (8)	C9—H9A	0.9700
N1—C8	1.484 (9)	C9—H9B	0.9700
N1—H1B	0.8599	C12—H12A	0.9600
O1—C13	1.248 (8)	C12—H12B	0.9600
O3—C14	1.239 (8)	C12—H12C	0.9600
O2—C13	1.266 (8)	C11—H11A	0.9600
O2—Zn1^iii	1.982 (5)	C11—H11B	0.9600
O4—C14	1.255 (8)	C11—H11C	0.9600
O4—Zn1^iv	1.989 (5)	C1—C2	1.355 (14)
C4—C5	1.379 (11)	C1—C6	1.370 (16)
C4—C3	1.374 (11)	C1—H1A	0.9300
C4—C7	1.514 (9)	C5—C6	1.381 (12)
C13—C8	1.516 (9)	C5—H5A	0.9300
C7—H7A	0.9700	C3—C2	1.376 (12)
C7—H7B	0.9700	C3—H3A	0.9300
C8—C9	1.531 (10)	C2—H2A	0.9300
C8—H8A	0.9800	C6—H6A	0.9300
O2^i—Zn1—O4^ii	101.5 (2)	O4—C14—H14A	116.2
O2^i—Zn1—O3	98.4 (2)	C12—C10—C11	111.5 (7)
O4^ii—Zn1—O3	103.6 (2)	C12—C10—C9	112.5 (7)
O2^i—Zn1—O1	91.3 (2)	C11—C10—C9	110.0 (7)
O4^ii—Zn1—O1	98.38 (18)	C12—C10—H10A	107.5
O3—Zn1—O1	153.55 (19)	C11—C10—H10A	107.5
O2^i—Zn1—N1	150.6 (2)	C9—C10—H10A	107.5
O4^ii—Zn1—N1	107.1 (2)	C8—C9—C10	115.6 (6)
O3—Zn1—N1	81.4 (2)	C8—C9—H9A	108.4
O1—Zn1—N1	78.3 (2)	C10—C9—H9A	108.4
C7—N1—C8	113.1 (5)	C8—C9—H9B	108.4
C7—N1—Zn1	108.1 (4)	C10—C9—H9B	108.4
C8—N1—Zn1	109.5 (4)	H9A—C9—H9B	107.4
C7—N1—H1B	107.9	C10—C12—H12A	109.5
C8—N1—H1B	109.0	C10—C12—H12B	109.5
Zn1—N1—H1B	109.1	H12A—C12—H12B	109.5
C13—O1—Zn1	115.8 (5)	C10—C12—H12C	109.5
C14—O3—Zn1	124.9 (5)	H12A—C12—H12C	109.5
C13—O2—Zn1^iii	113.5 (4)	H12B—C12—H12C	109.5
C14—O4—Zn1^iv	118.4 (5)	C10—C11—H11A	109.5
C5—C4—C3	117.9 (7)	C10—C11—H11B	109.5
C5—C4—C7	120.9 (7)	H11A—C11—H11B	109.5
C3—C4—C7	121.1 (7)	C10—C11—H11C	109.5
O1—C13—O2	124.8 (7)	H11A—C11—H11C	109.5
O1—C13—C8	119.8 (7)	H11B—C11—H11C	109.5
O2—C13—C8	115.4 (6)	C2—C1—C6	120.7 (9)
N1—C7—C4	114.4 (6)	C2—C1—H1A	119.7
N1—C7—H7A	108.7	C6—C1—H1A	119.7
C4—C7—H7A	108.7	C4—C5—C6	121.1 (9)
N1—C7—H7B	108.7	C4—C5—H5A	119.5
C4—C7—H7B	108.7	C6—C5—H5A	119.5
H7A—C7—H7B	107.6	C2—C3—C4	121.4 (9)
N1—C8—C9	110.3 (5)	C2—C3—H3A	119.3
N1—C8—C13	109.3 (5)	C4—C3—H3A	119.3
C9—C8—C13	110.0 (6)	C1—C2—C3	119.7 (10)
N1—C8—H8A	109.1	C1—C2—H2A	120.2
C9—C8—H8A	109.1	C3—C2—H2A	120.2
C13—C8—H8A	109.1	C1—C6—C5	119.2 (9)
O3—C14—O4	127.6 (7)	C1—C6—H6A	120.4
O3—C14—H14A	116.2	C5—C6—H6A	120.4

Symmetry codes: (i) x−1/2, −y+1/2, −z; (ii) x+1/2, −y+3/2, −z; (iii) x+1/2, −y+1/2, −z; (iv) x−1/2, −y+3/2, −z.