Bis[2-(cyclo­hexyl­imino­meth­yl)-4-nitro­phenolato]zinc(II)

In the mononuclear title compound, [Zn(C₁₃H₁₅N₂O₃)₂], the Zn^II atom is four-coordinated in a distorted tetra­hedral configuration by two imine N and two phenolate O atoms from two Schiff base ligands.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C)= 0.004 Å
• R factor = 0.047
• wR factor = 0.108
• Data-to-parameter ratio = 17.4

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Bis[2-(cyclohexyliminomethyl)-4-nitrophenolato]zinc(II)

Crystal data

[Zn(C13H15N2O3)2]	Z = 2
Mr = 559.91	F(000) = 584
Triclinic, P1	Dx = 1.443 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.759 (1) Å	Cell parameters from 4267 reflections
b = 11.108 (1) Å	θ = 2.3–25.5°
c = 12.439 (1) Å	µ = 1.00 mm^−1
α = 113.74 (1)°	T = 298 K
β = 104.39 (1)°	Block, colourless
γ = 94.99 (1)°	0.21 × 0.12 × 0.11 mm
V = 1288.5 (2) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	5819 independent reflections
Radiation source: fine-focus sealed tube	4828 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.817, Tmax = 0.898	k = −14→14
14907 measured reflections	l = −16→16

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.108	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0471P)^2 + 0.1392P] where P = (Fo^2 + 2Fc^2)/3
5819 reflections	(Δ/σ)max = 0.001
334 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.35 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
Zn1	0.03414 (3)	0.20850 (3)	0.40418 (3)	0.04017 (11)
O1	0.14419 (17)	0.33370 (17)	0.56775 (15)	0.0467 (4)
O2	−0.14807 (17)	0.14646 (19)	0.37687 (17)	0.0488 (4)
O3	0.64779 (19)	0.1822 (2)	0.8072 (2)	0.0723 (6)
O4	0.6737 (2)	0.3863 (2)	0.9419 (2)	0.0759 (7)
O5	−0.68835 (19)	0.1026 (2)	0.0253 (2)	0.0702 (6)
O6	−0.5669 (2)	0.2242 (3)	−0.0238 (2)	0.0726 (6)
N1	0.13635 (19)	0.06345 (19)	0.38532 (17)	0.0380 (5)
N2	0.00618 (18)	0.30055 (19)	0.29377 (17)	0.0355 (4)
N3	0.6126 (2)	0.2899 (3)	0.8442 (2)	0.0522 (6)
N4	−0.5820 (2)	0.1616 (2)	0.0351 (2)	0.0515 (6)
C1	0.2542 (2)	0.3186 (2)	0.6273 (2)	0.0379 (5)
C2	0.3282 (3)	0.4245 (3)	0.7426 (2)	0.0487 (6)
H2	0.2967	0.5030	0.7719	0.058*
C3	0.4436 (3)	0.4172 (3)	0.8132 (2)	0.0484 (6)
H3	0.4895	0.4889	0.8892	0.058*
C4	0.4914 (2)	0.3007 (3)	0.7697 (2)	0.0413 (6)
C5	0.4255 (2)	0.1959 (2)	0.6570 (2)	0.0410 (6)
H5	0.4605	0.1196	0.6289	0.049*
C6	0.3064 (2)	0.2013 (2)	0.5833 (2)	0.0368 (5)
C7	0.2443 (2)	0.0831 (2)	0.4681 (2)	0.0401 (6)
H7	0.2882	0.0124	0.4520	0.048*
C8	0.0933 (2)	−0.0698 (2)	0.2772 (2)	0.0415 (6)
H8	0.1716	−0.1067	0.2683	0.050*
C9	0.0305 (3)	−0.0576 (3)	0.1607 (2)	0.0624 (8)
H9A	0.0921	0.0014	0.1488	0.075*
H9B	−0.0459	−0.0183	0.1679	0.075*
C10	−0.0106 (3)	−0.1949 (3)	0.0500 (3)	0.0672 (9)
H10A	−0.0559	−0.1857	−0.0232	0.081*
H10B	0.0672	−0.2289	0.0373	0.081*
C11	−0.0986 (3)	−0.2942 (3)	0.0664 (3)	0.0651 (9)
H11A	−0.1163	−0.3820	−0.0031	0.078*
H11B	−0.1816	−0.2668	0.0678	0.078*
C12	−0.0364 (3)	−0.3040 (3)	0.1849 (3)	0.0646 (8)
H12A	0.0405	−0.3426	0.1790	0.077*
H12B	−0.0981	−0.3634	0.1962	0.077*
C13	0.0036 (3)	−0.1655 (3)	0.2970 (3)	0.0589 (8)
H13A	−0.0741	−0.1305	0.3084	0.071*
H13B	0.0481	−0.1739	0.3709	0.071*
C14	−0.2452 (2)	0.1538 (2)	0.2961 (2)	0.0407 (6)
C15	−0.3735 (3)	0.0951 (3)	0.2816 (3)	0.0548 (7)
H15	−0.3848	0.0536	0.3312	0.066*
C16	−0.4815 (3)	0.0968 (3)	0.1979 (3)	0.0531 (7)
H16	−0.5647	0.0570	0.1908	0.064*
C17	−0.4664 (2)	0.1580 (2)	0.1238 (2)	0.0414 (6)
C18	−0.3448 (2)	0.2167 (2)	0.1331 (2)	0.0399 (6)
H18	−0.3369	0.2569	0.0817	0.048*
C19	−0.2317 (2)	0.2175 (2)	0.2188 (2)	0.0361 (5)
C20	−0.1097 (2)	0.2882 (2)	0.2251 (2)	0.0369 (5)
H20	−0.1154	0.3301	0.1732	0.044*
C21	0.1154 (2)	0.3878 (2)	0.2910 (2)	0.0378 (5)
H21	0.0897	0.3926	0.2118	0.045*
C22	0.2376 (2)	0.3284 (3)	0.3001 (3)	0.0450 (6)
H22A	0.2600	0.3155	0.3747	0.054*
H22B	0.2197	0.2411	0.2299	0.054*
C23	0.3527 (3)	0.4199 (3)	0.3025 (3)	0.0533 (7)
H23A	0.4304	0.3823	0.3130	0.064*
H23B	0.3339	0.4257	0.2246	0.064*
C24	0.3782 (3)	0.5590 (3)	0.4072 (3)	0.0531 (7)
H24A	0.4030	0.5539	0.4855	0.064*
H24B	0.4504	0.6168	0.4062	0.064*
C25	0.2574 (3)	0.6187 (3)	0.3953 (3)	0.0538 (7)
H25A	0.2362	0.6295	0.3197	0.065*
H25B	0.2751	0.7069	0.4642	0.065*
C26	0.1410 (2)	0.5289 (2)	0.3936 (2)	0.0462 (6)
H26A	0.1587	0.5254	0.4725	0.055*
H26B	0.0636	0.5666	0.3813	0.055*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.03783 (17)	0.04605 (19)	0.03779 (17)	0.01433 (13)	0.00743 (12)	0.02098 (13)
O1	0.0490 (10)	0.0459 (10)	0.0389 (9)	0.0212 (8)	0.0057 (8)	0.0149 (8)
O2	0.0392 (10)	0.0608 (12)	0.0538 (11)	0.0090 (8)	0.0076 (8)	0.0366 (10)
O3	0.0449 (12)	0.0876 (17)	0.0782 (16)	0.0247 (11)	0.0061 (11)	0.0359 (13)
O4	0.0523 (12)	0.0817 (16)	0.0614 (14)	−0.0029 (11)	−0.0158 (11)	0.0231 (12)
O5	0.0325 (11)	0.0760 (15)	0.0858 (16)	0.0052 (10)	0.0012 (10)	0.0310 (13)
O6	0.0489 (12)	0.0994 (18)	0.0767 (15)	0.0204 (12)	0.0046 (11)	0.0535 (14)
N1	0.0400 (11)	0.0380 (11)	0.0338 (10)	0.0113 (9)	0.0098 (9)	0.0139 (9)
N2	0.0336 (10)	0.0380 (11)	0.0344 (10)	0.0088 (8)	0.0092 (8)	0.0161 (9)
N3	0.0351 (12)	0.0661 (16)	0.0543 (15)	0.0056 (11)	0.0063 (11)	0.0310 (13)
N4	0.0358 (13)	0.0493 (13)	0.0529 (14)	0.0123 (10)	0.0033 (10)	0.0120 (11)
C1	0.0389 (13)	0.0394 (13)	0.0353 (12)	0.0100 (11)	0.0100 (10)	0.0169 (11)
C2	0.0535 (16)	0.0433 (15)	0.0410 (14)	0.0152 (12)	0.0107 (12)	0.0120 (12)
C3	0.0489 (15)	0.0457 (15)	0.0366 (14)	0.0001 (12)	0.0058 (12)	0.0111 (12)
C4	0.0342 (13)	0.0505 (15)	0.0393 (13)	0.0043 (11)	0.0055 (10)	0.0241 (12)
C5	0.0385 (13)	0.0412 (14)	0.0447 (14)	0.0107 (11)	0.0113 (11)	0.0205 (12)
C6	0.0366 (13)	0.0378 (13)	0.0349 (12)	0.0088 (10)	0.0078 (10)	0.0166 (10)
C7	0.0405 (13)	0.0402 (13)	0.0393 (13)	0.0151 (11)	0.0115 (11)	0.0164 (11)
C8	0.0411 (13)	0.0415 (14)	0.0335 (12)	0.0128 (11)	0.0072 (10)	0.0102 (11)
C9	0.089 (2)	0.0486 (17)	0.0344 (14)	0.0010 (16)	0.0062 (15)	0.0143 (13)
C10	0.091 (2)	0.0573 (19)	0.0340 (15)	0.0066 (17)	0.0034 (15)	0.0128 (13)
C11	0.0575 (18)	0.0503 (17)	0.0568 (18)	0.0076 (14)	−0.0032 (15)	0.0069 (15)
C12	0.078 (2)	0.0469 (17)	0.0574 (18)	0.0011 (15)	0.0152 (16)	0.0171 (15)
C13	0.076 (2)	0.0488 (17)	0.0451 (16)	0.0057 (15)	0.0168 (15)	0.0169 (13)
C14	0.0384 (13)	0.0396 (13)	0.0408 (14)	0.0075 (11)	0.0087 (11)	0.0169 (11)
C15	0.0456 (16)	0.0582 (18)	0.0676 (19)	0.0025 (13)	0.0129 (14)	0.0389 (16)
C16	0.0361 (14)	0.0507 (16)	0.0656 (18)	0.0000 (12)	0.0099 (13)	0.0241 (14)
C17	0.0349 (13)	0.0376 (13)	0.0424 (14)	0.0087 (10)	0.0053 (11)	0.0123 (11)
C18	0.0395 (13)	0.0370 (13)	0.0385 (13)	0.0094 (11)	0.0061 (11)	0.0151 (11)
C19	0.0354 (12)	0.0328 (12)	0.0354 (12)	0.0084 (10)	0.0079 (10)	0.0120 (10)
C20	0.0390 (13)	0.0390 (13)	0.0348 (12)	0.0120 (10)	0.0111 (10)	0.0177 (10)
C21	0.0346 (12)	0.0429 (14)	0.0358 (12)	0.0062 (10)	0.0078 (10)	0.0195 (11)
C22	0.0384 (14)	0.0456 (15)	0.0501 (15)	0.0110 (11)	0.0164 (12)	0.0183 (12)
C23	0.0358 (14)	0.0700 (19)	0.0545 (17)	0.0139 (13)	0.0168 (12)	0.0255 (15)
C24	0.0382 (14)	0.0633 (18)	0.0522 (17)	−0.0024 (13)	0.0071 (12)	0.0266 (15)
C25	0.0532 (17)	0.0456 (16)	0.0572 (17)	0.0040 (13)	0.0151 (14)	0.0198 (13)
C26	0.0418 (14)	0.0455 (15)	0.0495 (15)	0.0123 (11)	0.0160 (12)	0.0173 (12)

Geometric parameters (Å, º)

Zn1—O2	1.918 (2)	C11—C12	1.511 (4)
Zn1—O1	1.927 (2)	C11—H11A	0.97
Zn1—N1	1.998 (2)	C11—H11B	0.97
Zn1—N2	2.000 (2)	C12—C13	1.535 (4)
O1—C1	1.295 (3)	C12—H12A	0.97
O2—C14	1.292 (3)	C12—H12B	0.97
O3—N3	1.228 (3)	C13—H13A	0.97
O4—N3	1.220 (3)	C13—H13B	0.97
O5—N4	1.220 (3)	C14—C15	1.411 (4)
O6—N4	1.224 (3)	C14—C19	1.430 (3)
N1—C7	1.280 (3)	C15—C16	1.360 (4)
N1—C8	1.477 (3)	C15—H15	0.93
N2—C20	1.284 (3)	C16—C17	1.379 (4)
N2—C21	1.473 (3)	C16—H16	0.93
N3—C4	1.446 (3)	C17—C18	1.366 (3)
N4—C17	1.459 (3)	C18—C19	1.401 (3)
C1—C2	1.410 (3)	C18—H18	0.93
C1—C6	1.421 (3)	C19—C20	1.437 (3)
C2—C3	1.361 (4)	C20—H20	0.93
C2—H2	0.93	C21—C26	1.517 (3)
C3—C4	1.386 (4)	C21—C22	1.521 (3)
C3—H3	0.93	C21—H21	0.98
C4—C5	1.367 (3)	C22—C23	1.518 (4)
C5—C6	1.400 (3)	C22—H22A	0.97
C5—H5	0.93	C22—H22B	0.97
C6—C7	1.442 (3)	C23—C24	1.513 (4)
C7—H7	0.93	C23—H23A	0.97
C8—C9	1.504 (4)	C23—H23B	0.97
C8—C13	1.508 (4)	C24—C25	1.511 (4)
C8—H8	0.98	C24—H24A	0.97
C9—C10	1.518 (4)	C24—H24B	0.97
C9—H9A	0.97	C25—C26	1.522 (4)
C9—H9B	0.97	C25—H25A	0.97
C10—C11	1.500 (4)	C25—H25B	0.97
C10—H10A	0.97	C26—H26A	0.97
C10—H10B	0.97	C26—H26B	0.97
O2—Zn1—O1	119.44 (8)	C13—C12—H12A	109.3
O2—Zn1—N1	112.74 (8)	C11—C12—H12B	109.3
O1—Zn1—N1	96.25 (7)	C13—C12—H12B	109.3
O2—Zn1—N2	96.40 (7)	H12A—C12—H12B	108.0
O1—Zn1—N2	109.86 (8)	C8—C13—C12	109.9 (2)
N1—Zn1—N2	123.95 (8)	C8—C13—H13A	109.7
C1—O1—Zn1	125.67 (15)	C12—C13—H13A	109.7
C14—O2—Zn1	125.52 (17)	C8—C13—H13B	109.7
C7—N1—C8	116.7 (2)	C12—C13—H13B	109.7
C7—N1—Zn1	120.59 (16)	H13A—C13—H13B	108.2
C8—N1—Zn1	122.72 (15)	O2—C14—C15	118.6 (2)
C20—N2—C21	117.7 (2)	O2—C14—C19	124.3 (2)
C20—N2—Zn1	120.46 (16)	C15—C14—C19	117.1 (2)
C21—N2—Zn1	121.84 (14)	C16—C15—C14	122.7 (3)
O4—N3—O3	122.9 (2)	C16—C15—H15	118.7
O4—N3—C4	119.0 (2)	C14—C15—H15	118.7
O3—N3—C4	118.1 (2)	C15—C16—C17	119.3 (2)
O5—N4—O6	124.1 (2)	C15—C16—H16	120.3
O5—N4—C17	117.6 (3)	C17—C16—H16	120.3
O6—N4—C17	118.3 (2)	C18—C17—C16	121.0 (2)
O1—C1—C2	118.6 (2)	C18—C17—N4	119.5 (2)
O1—C1—C6	124.0 (2)	C16—C17—N4	119.5 (2)
C2—C1—C6	117.3 (2)	C17—C18—C19	121.1 (2)
C3—C2—C1	123.0 (2)	C17—C18—H18	119.4
C3—C2—H2	118.5	C19—C18—H18	119.4
C1—C2—H2	118.5	C18—C19—C14	118.8 (2)
C2—C3—C4	118.7 (2)	C18—C19—C20	116.3 (2)
C2—C3—H3	120.7	C14—C19—C20	124.8 (2)
C4—C3—H3	120.7	N2—C20—C19	127.8 (2)
C5—C4—C3	120.9 (2)	N2—C20—H20	116.1
C5—C4—N3	119.6 (2)	C19—C20—H20	116.1
C3—C4—N3	119.6 (2)	N2—C21—C26	110.16 (19)
C4—C5—C6	121.3 (2)	N2—C21—C22	110.44 (19)
C4—C5—H5	119.4	C26—C21—C22	111.6 (2)
C6—C5—H5	119.4	N2—C21—H21	108.2
C5—C6—C1	118.8 (2)	C26—C21—H21	108.2
C5—C6—C7	116.1 (2)	C22—C21—H21	108.2
C1—C6—C7	125.0 (2)	C23—C22—C21	111.2 (2)
N1—C7—C6	128.0 (2)	C23—C22—H22A	109.4
N1—C7—H7	116.0	C21—C22—H22A	109.4
C6—C7—H7	116.0	C23—C22—H22B	109.4
N1—C8—C9	111.0 (2)	C21—C22—H22B	109.4
N1—C8—C13	111.0 (2)	H22A—C22—H22B	108.0
C9—C8—C13	111.7 (2)	C24—C23—C22	110.5 (2)
N1—C8—H8	107.6	C24—C23—H23A	109.5
C9—C8—H8	107.6	C22—C23—H23A	109.5
C13—C8—H8	107.6	C24—C23—H23B	109.5
C8—C9—C10	110.4 (2)	C22—C23—H23B	109.5
C8—C9—H9A	109.6	H23A—C23—H23B	108.1
C10—C9—H9A	109.6	C25—C24—C23	110.7 (2)
C8—C9—H9B	109.6	C25—C24—H24A	109.5
C10—C9—H9B	109.6	C23—C24—H24A	109.5
H9A—C9—H9B	108.1	C25—C24—H24B	109.5
C11—C10—C9	112.3 (3)	C23—C24—H24B	109.5
C11—C10—H10A	109.1	H24A—C24—H24B	108.1
C9—C10—H10A	109.1	C24—C25—C26	111.0 (2)
C11—C10—H10B	109.1	C24—C25—H25A	109.4
C9—C10—H10B	109.1	C26—C25—H25A	109.4
H10A—C10—H10B	107.9	C24—C25—H25B	109.4
C10—C11—C12	111.2 (2)	C26—C25—H25B	109.4
C10—C11—H11A	109.4	H25A—C25—H25B	108.0
C12—C11—H11A	109.4	C21—C26—C25	110.7 (2)
C10—C11—H11B	109.4	C21—C26—H26A	109.5
C12—C11—H11B	109.4	C25—C26—H26A	109.5
H11A—C11—H11B	108.0	C21—C26—H26B	109.5
C11—C12—C13	111.5 (3)	C25—C26—H26B	109.5
C11—C12—H12A	109.3	H26A—C26—H26B	108.1
O2—Zn1—O1—C1	127.08 (19)	Zn1—N1—C8—C13	−87.8 (2)
N1—Zn1—O1—C1	6.5 (2)	N1—C8—C9—C10	178.8 (2)
N2—Zn1—O1—C1	−123.0 (2)	C13—C8—C9—C10	−56.7 (3)
O1—Zn1—O2—C14	125.3 (2)	C8—C9—C10—C11	55.1 (4)
N1—Zn1—O2—C14	−122.8 (2)	C9—C10—C11—C12	−54.4 (4)
N2—Zn1—O2—C14	8.2 (2)	C10—C11—C12—C13	54.6 (4)
O2—Zn1—N1—C7	−130.76 (19)	N1—C8—C13—C12	−178.4 (2)
O1—Zn1—N1—C7	−5.2 (2)	C9—C8—C13—C12	57.1 (3)
N2—Zn1—N1—C7	113.89 (19)	C11—C12—C13—C8	−55.7 (4)
O2—Zn1—N1—C8	49.53 (19)	Zn1—O2—C14—C15	175.68 (19)
O1—Zn1—N1—C8	175.12 (18)	Zn1—O2—C14—C19	−4.0 (3)
N2—Zn1—N1—C8	−65.8 (2)	O2—C14—C15—C16	−179.3 (3)
O2—Zn1—N2—C20	−7.44 (19)	C19—C14—C15—C16	0.4 (4)
O1—Zn1—N2—C20	−131.94 (17)	C14—C15—C16—C17	−0.1 (5)
N1—Zn1—N2—C20	115.55 (18)	C15—C16—C17—C18	0.1 (4)
O2—Zn1—N2—C21	170.43 (17)	C15—C16—C17—N4	−179.2 (2)
O1—Zn1—N2—C21	45.93 (18)	O5—N4—C17—C18	176.6 (2)
N1—Zn1—N2—C21	−66.57 (19)	O6—N4—C17—C18	−4.0 (4)
Zn1—O1—C1—C2	175.13 (18)	O5—N4—C17—C16	−4.1 (4)
Zn1—O1—C1—C6	−4.5 (3)	O6—N4—C17—C16	175.2 (3)
O1—C1—C2—C3	178.6 (3)	C16—C17—C18—C19	−0.5 (4)
C6—C1—C2—C3	−1.7 (4)	N4—C17—C18—C19	178.8 (2)
C1—C2—C3—C4	0.4 (4)	C17—C18—C19—C14	0.8 (3)
C2—C3—C4—C5	1.2 (4)	C17—C18—C19—C20	−176.8 (2)
C2—C3—C4—N3	−178.9 (2)	O2—C14—C19—C18	178.9 (2)
O4—N3—C4—C5	176.6 (2)	C15—C14—C19—C18	−0.8 (3)
O3—N3—C4—C5	−5.0 (4)	O2—C14—C19—C20	−3.7 (4)
O4—N3—C4—C3	−3.3 (4)	C15—C14—C19—C20	176.7 (2)
O3—N3—C4—C3	175.0 (2)	C21—N2—C20—C19	−175.1 (2)
C3—C4—C5—C6	−1.5 (4)	Zn1—N2—C20—C19	2.9 (3)
N3—C4—C5—C6	178.6 (2)	C18—C19—C20—N2	−178.4 (2)
C4—C5—C6—C1	0.2 (4)	C14—C19—C20—N2	4.1 (4)
C4—C5—C6—C7	−178.2 (2)	C20—N2—C21—C26	93.5 (2)
O1—C1—C6—C5	−179.0 (2)	Zn1—N2—C21—C26	−84.4 (2)
C2—C1—C6—C5	1.3 (4)	C20—N2—C21—C22	−142.8 (2)
O1—C1—C6—C7	−0.7 (4)	Zn1—N2—C21—C22	39.3 (2)
C2—C1—C6—C7	179.6 (2)	N2—C21—C22—C23	−177.7 (2)
C8—N1—C7—C6	−178.1 (2)	C26—C21—C22—C23	−54.9 (3)
Zn1—N1—C7—C6	2.1 (4)	C21—C22—C23—C24	56.1 (3)
C5—C6—C7—N1	−179.8 (2)	C22—C23—C24—C25	−57.7 (3)
C1—C6—C7—N1	1.9 (4)	C23—C24—C25—C26	57.8 (3)
C7—N1—C8—C9	−142.6 (3)	N2—C21—C26—C25	177.6 (2)
Zn1—N1—C8—C9	37.1 (3)	C22—C21—C26—C25	54.5 (3)
C7—N1—C8—C13	92.4 (3)	C24—C25—C26—C21	−56.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O3^i	0.98	2.43	3.380 (3)	163
C24—H24B···Cg1^ii	0.97	2.78	3.680 (4)	155

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