Pyridine­{4,4',6,6'-tetra­bromo-2,2'-[1,2-phenyl­enebis(nitrilo­methyl­idyne)]diphenolato}zinc(II) dimethyl­formamide solvate

The tetra­dentate Schiff base ligand derived from the condensation of 3,5-dibromo­salicylaldehyde and 1,2-phenyl­enediamine, in the presence of pyridine, forms a square-pyramidal five-coordinate Zn complex, [Zn(C₂₀H₁₀Br₄N₂O₂)(C₅H₅N)]·C₃H₇N0.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.045
• wR factor = 0.162
• Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N4
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9

   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
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2001); program(s) used to refine structure: SHELXL97 (Sheldrick, 2001); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

Pyridine{4,4',6,6'-tetrabromo-2,2'-[1,2- phenylenebis(nitrilomethylidyne)]diphenolato}zinc(II) dimethylformamide solvate

Crystal data

[Zn(C20H10Br4N2O2)(C5H5N)]·C3H7N0	F(000) = 1648
Mr = 847.51	Dx = 1.892 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3507 reflections
a = 8.2289 (9) Å	θ = 2.5–22.7°
b = 15.2809 (17) Å	µ = 6.23 mm^−1
c = 23.793 (3) Å	T = 292 K
β = 95.946 (2)°	Block, yellow
V = 2975.7 (6) Å^3	0.20 × 0.20 × 0.18 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	5823 independent reflections
Radiation source: fine-focus sealed tube	3982 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
φ and ω scans	θmax = 26.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→9
Tmin = 0.300, Tmax = 0.326	k = −18→18
15973 measured reflections	l = −26→29

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.162	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0926P)^2] where P = (Fo^2 + 2Fc^2)/3
5823 reflections	(Δ/σ)max = 0.002
363 parameters	Δρmax = 0.72 e Å^−3
0 restraints	Δρmin = −0.83 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	0.06400 (7)	0.99760 (4)	0.24197 (3)	0.03503 (19)
Br4	0.36814 (8)	1.27491 (5)	0.26138 (3)	0.0579 (2)
Br1	0.31966 (10)	1.00646 (5)	0.43821 (3)	0.0657 (2)
Br3	0.11034 (13)	1.37468 (5)	0.04282 (3)	0.0819 (3)
Br2	0.49434 (11)	0.65040 (5)	0.42411 (3)	0.0756 (3)
N1	0.0754 (5)	0.8631 (3)	0.22384 (19)	0.0363 (10)
N2	0.0021 (6)	0.9941 (3)	0.15314 (19)	0.0405 (11)
N3	−0.1608 (5)	1.0261 (3)	0.2705 (2)	0.0398 (11)
N4	0.3378 (8)	0.8600 (5)	0.0802 (3)	0.0713 (17)
O1	0.1804 (5)	0.9734 (3)	0.31802 (16)	0.0435 (10)
O2	0.1701 (5)	1.1122 (3)	0.23234 (16)	0.0439 (10)
O3	0.2215 (13)	0.9618 (9)	0.0255 (4)	0.199 (6)
C1	0.2398 (6)	0.9021 (4)	0.3396 (2)	0.0391 (13)
C2	0.3181 (7)	0.9013 (4)	0.3961 (2)	0.0463 (15)
C3	0.3929 (7)	0.8298 (4)	0.4209 (3)	0.0520 (16)
H3	0.4463	0.8334	0.4573	0.062*
C4	0.3884 (7)	0.7509 (4)	0.3911 (3)	0.0492 (16)
C5	0.3099 (8)	0.7468 (4)	0.3374 (3)	0.0482 (15)
H5	0.3063	0.6939	0.3179	0.058*
C6	0.2348 (7)	0.8211 (4)	0.3112 (2)	0.0385 (13)
C7	0.1540 (7)	0.8068 (4)	0.2555 (2)	0.0455 (14)
H7	0.1596	0.7505	0.2409	0.055*
C8	−0.0066 (7)	0.8413 (4)	0.1702 (2)	0.0402 (13)
C9	−0.0498 (9)	0.7553 (4)	0.1545 (3)	0.0532 (16)
H9	−0.0231	0.7087	0.1788	0.064*
C10	−0.1330 (9)	0.7415 (4)	0.1017 (3)	0.0599 (18)
H10	−0.1613	0.6847	0.0906	0.072*
C11	−0.1749 (9)	0.8092 (5)	0.0653 (3)	0.0635 (19)
H11	−0.2314	0.7983	0.0301	0.076*
C12	−0.1330 (8)	0.8928 (5)	0.0812 (3)	0.0566 (17)
H12	−0.1614	0.9386	0.0564	0.068*
C13	−0.0486 (7)	0.9109 (4)	0.1338 (2)	0.0418 (13)
C14	0.0101 (7)	1.0598 (4)	0.1196 (2)	0.0392 (13)
H14	−0.0284	1.0513	0.0819	0.047*
C15	0.0733 (7)	1.1456 (4)	0.1353 (3)	0.0409 (13)
C16	0.0600 (8)	1.2094 (4)	0.0928 (3)	0.0485 (15)
H16	0.0010	1.1970	0.0583	0.058*
C17	0.1305 (8)	1.2878 (4)	0.1010 (3)	0.0533 (17)
C18	0.2219 (8)	1.3078 (4)	0.1511 (3)	0.0566 (17)
H18	0.2739	1.3617	0.1560	0.068*
C19	0.2349 (7)	1.2469 (4)	0.1935 (2)	0.0399 (13)
C20	0.1580 (6)	1.1636 (4)	0.1897 (2)	0.0377 (13)
C21	−0.1717 (7)	1.0396 (4)	0.3254 (3)	0.0466 (14)
H21	−0.0768	1.0385	0.3502	0.056*
C22	−0.3201 (9)	1.0553 (4)	0.3468 (3)	0.0614 (19)
H22	−0.3247	1.0618	0.3854	0.074*
C23	−0.4593 (9)	1.0608 (5)	0.3100 (4)	0.068 (2)
H23	−0.5595	1.0728	0.3232	0.081*
C24	−0.4485 (8)	1.0485 (5)	0.2536 (4)	0.066 (2)
H24	−0.5414	1.0520	0.2279	0.080*
C25	−0.2979 (7)	1.0308 (4)	0.2353 (3)	0.0514 (16)
H25	−0.2918	1.0218	0.1969	0.062*
C26	0.3520 (16)	0.7689 (7)	0.0880 (6)	0.144 (5)
H26A	0.3083	0.7528	0.1224	0.215*
H26B	0.4650	0.7524	0.0902	0.215*
H26C	0.2923	0.7394	0.0567	0.215*
C27	0.4172 (14)	0.9096 (9)	0.1232 (5)	0.133 (4)
H27A	0.5330	0.9067	0.1211	0.199*
H27B	0.3923	0.8872	0.1590	0.199*
H27C	0.3815	0.9693	0.1193	0.199*
C28	0.2523 (14)	0.8949 (12)	0.0389 (5)	0.149 (7)
H28	0.2041	0.8536	0.0138	0.179*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0366 (3)	0.0340 (4)	0.0344 (4)	0.0009 (3)	0.0032 (3)	0.0004 (3)
Br4	0.0640 (4)	0.0531 (4)	0.0567 (4)	−0.0161 (3)	0.0069 (3)	−0.0110 (3)
Br1	0.0848 (5)	0.0630 (5)	0.0458 (4)	0.0135 (4)	−0.0103 (4)	−0.0110 (3)
Br3	0.1443 (8)	0.0469 (4)	0.0567 (5)	−0.0017 (5)	0.0201 (5)	0.0163 (4)
Br2	0.0937 (6)	0.0608 (5)	0.0715 (5)	0.0280 (4)	0.0045 (4)	0.0255 (4)
N1	0.041 (3)	0.031 (3)	0.038 (3)	−0.001 (2)	0.008 (2)	−0.004 (2)
N2	0.039 (3)	0.052 (3)	0.030 (3)	−0.006 (2)	0.003 (2)	−0.001 (2)
N3	0.037 (3)	0.032 (3)	0.051 (3)	0.0065 (19)	0.008 (2)	0.000 (2)
N4	0.071 (4)	0.076 (5)	0.066 (4)	−0.002 (3)	0.001 (3)	0.013 (4)
O1	0.052 (2)	0.037 (2)	0.040 (2)	0.0061 (18)	−0.0061 (18)	−0.0038 (18)
O2	0.047 (2)	0.044 (2)	0.040 (2)	−0.0071 (18)	−0.0002 (18)	0.0049 (19)
O3	0.181 (9)	0.298 (14)	0.131 (7)	0.134 (9)	0.072 (7)	0.136 (9)
C1	0.032 (3)	0.050 (4)	0.035 (3)	0.008 (2)	0.003 (2)	0.004 (3)
C2	0.042 (3)	0.056 (4)	0.041 (3)	0.009 (3)	0.006 (3)	−0.003 (3)
C3	0.054 (4)	0.059 (4)	0.043 (4)	0.015 (3)	0.003 (3)	0.008 (3)
C4	0.054 (4)	0.047 (4)	0.048 (4)	0.018 (3)	0.011 (3)	0.017 (3)
C5	0.062 (4)	0.034 (3)	0.050 (4)	0.012 (3)	0.016 (3)	0.000 (3)
C6	0.042 (3)	0.035 (3)	0.040 (3)	0.006 (2)	0.009 (2)	0.007 (3)
C7	0.055 (4)	0.046 (4)	0.036 (3)	0.004 (3)	0.009 (3)	−0.002 (3)
C8	0.047 (3)	0.039 (3)	0.035 (3)	−0.006 (3)	0.008 (3)	−0.005 (3)
C9	0.077 (4)	0.026 (3)	0.057 (4)	−0.010 (3)	0.007 (3)	−0.006 (3)
C10	0.092 (5)	0.033 (3)	0.053 (4)	−0.022 (3)	0.003 (4)	−0.012 (3)
C11	0.078 (5)	0.063 (5)	0.047 (4)	−0.024 (4)	−0.005 (3)	−0.012 (4)
C12	0.068 (4)	0.062 (5)	0.038 (4)	−0.015 (3)	−0.001 (3)	0.001 (3)
C13	0.045 (3)	0.045 (4)	0.036 (3)	−0.006 (3)	0.006 (3)	−0.006 (3)
C14	0.046 (3)	0.035 (3)	0.036 (3)	−0.004 (2)	0.000 (2)	−0.001 (3)
C15	0.046 (3)	0.033 (3)	0.045 (3)	−0.002 (2)	0.009 (3)	0.003 (3)
C16	0.058 (4)	0.049 (4)	0.039 (3)	−0.004 (3)	0.009 (3)	0.007 (3)
C17	0.075 (4)	0.044 (4)	0.044 (4)	0.004 (3)	0.021 (3)	0.012 (3)
C18	0.070 (4)	0.044 (4)	0.061 (4)	−0.005 (3)	0.029 (4)	−0.004 (3)
C19	0.048 (3)	0.031 (3)	0.042 (3)	−0.001 (2)	0.009 (3)	−0.003 (3)
C20	0.039 (3)	0.032 (3)	0.044 (3)	−0.001 (2)	0.015 (3)	−0.002 (3)
C21	0.051 (4)	0.037 (3)	0.053 (4)	0.006 (3)	0.010 (3)	0.005 (3)
C22	0.076 (5)	0.044 (4)	0.070 (5)	0.004 (3)	0.037 (4)	0.000 (3)
C23	0.051 (4)	0.051 (4)	0.106 (6)	0.010 (3)	0.032 (4)	0.005 (4)
C24	0.041 (4)	0.060 (5)	0.097 (6)	0.004 (3)	0.004 (4)	−0.004 (4)
C25	0.040 (3)	0.045 (4)	0.069 (4)	0.003 (3)	0.004 (3)	−0.002 (3)
C26	0.140 (10)	0.086 (8)	0.215 (15)	−0.017 (7)	0.070 (10)	−0.008 (9)
C27	0.109 (8)	0.161 (12)	0.127 (10)	−0.003 (8)	0.002 (7)	0.027 (9)
C28	0.102 (8)	0.28 (2)	0.068 (7)	0.068 (11)	0.009 (6)	0.050 (10)

Geometric parameters (Å, º)

Zn1—O2	1.980 (4)	C9—H9	0.9300
Zn1—O1	1.993 (4)	C10—C11	1.369 (10)
Zn1—N3	2.082 (4)	C10—H10	0.9300
Zn1—N1	2.104 (4)	C11—C12	1.367 (10)
Zn1—N2	2.123 (5)	C11—H11	0.9300
Br4—C19	1.904 (6)	C12—C13	1.395 (8)
Br1—C2	1.893 (6)	C12—H12	0.9300
Br3—C17	1.913 (6)	C14—C15	1.444 (8)
Br2—C4	1.895 (6)	C14—H14	0.9300
N1—C7	1.275 (7)	C15—C16	1.400 (8)
N1—C8	1.420 (7)	C15—C20	1.434 (8)
N2—C14	1.289 (7)	C16—C17	1.337 (9)
N2—C13	1.401 (7)	C16—H16	0.9300
N3—C21	1.333 (7)	C17—C18	1.376 (9)
N3—C25	1.336 (7)	C18—C19	1.368 (8)
N4—C28	1.266 (11)	C18—H18	0.9300
N4—C27	1.381 (12)	C19—C20	1.420 (8)
N4—C26	1.407 (12)	C21—C22	1.391 (9)
O1—C1	1.279 (7)	C21—H21	0.9300
O2—C20	1.278 (6)	C22—C23	1.369 (10)
O3—C28	1.093 (17)	C22—H22	0.9300
C1—C6	1.410 (8)	C23—C24	1.367 (10)
C1—C2	1.430 (8)	C23—H23	0.9300
C2—C3	1.358 (8)	C24—C25	1.383 (9)
C3—C4	1.399 (9)	C24—H24	0.9300
C3—H3	0.9300	C25—H25	0.9300
C4—C5	1.373 (9)	C26—H26A	0.9600
C5—C6	1.406 (8)	C26—H26B	0.9600
C5—H5	0.9300	C26—H26C	0.9600
C6—C7	1.436 (8)	C27—H27A	0.9600
C7—H7	0.9300	C27—H27B	0.9600
C8—C13	1.393 (8)	C27—H27C	0.9600
C8—C9	1.402 (8)	C28—H28	0.9300
C9—C10	1.382 (9)
O2—Zn1—O1	95.34 (16)	C11—C12—C13	121.4 (7)
O2—Zn1—N3	105.65 (18)	C11—C12—H12	119.3
O1—Zn1—N3	95.87 (18)	C13—C12—H12	119.3
O2—Zn1—N1	144.13 (17)	C8—C13—C12	118.4 (6)
O1—Zn1—N1	88.70 (17)	C8—C13—N2	116.2 (5)
N3—Zn1—N1	109.37 (18)	C12—C13—N2	125.3 (6)
O2—Zn1—N2	88.31 (17)	N2—C14—C15	126.0 (5)
O1—Zn1—N2	160.50 (18)	N2—C14—H14	117.0
N3—Zn1—N2	101.58 (18)	C15—C14—H14	117.0
N1—Zn1—N2	77.42 (18)	C16—C15—C20	120.8 (5)
C7—N1—C8	122.4 (5)	C16—C15—C14	116.6 (5)
C7—N1—Zn1	124.7 (4)	C20—C15—C14	122.4 (5)
C8—N1—Zn1	112.8 (4)	C17—C16—C15	121.3 (6)
C14—N2—C13	122.5 (5)	C17—C16—H16	119.4
C14—N2—Zn1	125.0 (4)	C15—C16—H16	119.4
C13—N2—Zn1	112.5 (4)	C16—C17—C18	121.0 (6)
C21—N3—C25	117.9 (5)	C16—C17—Br3	120.9 (5)
C21—N3—Zn1	120.3 (4)	C18—C17—Br3	118.1 (5)
C25—N3—Zn1	121.8 (4)	C19—C18—C17	118.8 (6)
C28—N4—C27	121.7 (11)	C19—C18—H18	120.6
C28—N4—C26	123.5 (12)	C17—C18—H18	120.6
C27—N4—C26	114.7 (10)	C18—C19—C20	124.2 (6)
C1—O1—Zn1	130.6 (4)	C18—C19—Br4	117.9 (5)
C20—O2—Zn1	129.5 (3)	C20—C19—Br4	117.9 (4)
O1—C1—C6	124.3 (5)	O2—C20—C19	120.3 (5)
O1—C1—C2	120.1 (5)	O2—C20—C15	126.1 (5)
C6—C1—C2	115.6 (5)	C19—C20—C15	113.7 (5)
C3—C2—C1	123.7 (6)	N3—C21—C22	122.4 (6)
C3—C2—Br1	118.4 (5)	N3—C21—H21	118.8
C1—C2—Br1	117.9 (5)	C22—C21—H21	118.8
C2—C3—C4	119.1 (6)	C23—C22—C21	119.0 (7)
C2—C3—H3	120.4	C23—C22—H22	120.5
C4—C3—H3	120.4	C21—C22—H22	120.5
C5—C4—C3	119.8 (6)	C24—C23—C22	118.8 (6)
C5—C4—Br2	120.1 (5)	C24—C23—H23	120.6
C3—C4—Br2	120.1 (5)	C22—C23—H23	120.6
C4—C5—C6	121.3 (6)	C23—C24—C25	119.3 (7)
C4—C5—H5	119.4	C23—C24—H24	120.4
C6—C5—H5	119.4	C25—C24—H24	120.4
C5—C6—C1	120.4 (5)	N3—C25—C24	122.5 (7)
C5—C6—C7	115.2 (5)	N3—C25—H25	118.7
C1—C6—C7	124.3 (5)	C24—C25—H25	118.7
N1—C7—C6	126.9 (6)	N4—C26—H26A	109.5
N1—C7—H7	116.6	N4—C26—H26B	109.5
C6—C7—H7	116.6	H26A—C26—H26B	109.5
C13—C8—C9	120.6 (5)	N4—C26—H26C	109.5
C13—C8—N1	116.3 (5)	H26A—C26—H26C	109.5
C9—C8—N1	123.0 (5)	H26B—C26—H26C	109.5
C10—C9—C8	118.3 (6)	N4—C27—H27A	109.5
C10—C9—H9	120.9	N4—C27—H27B	109.5
C8—C9—H9	120.9	H27A—C27—H27B	109.5
C11—C10—C9	121.9 (6)	N4—C27—H27C	109.5
C11—C10—H10	119.1	H27A—C27—H27C	109.5
C9—C10—H10	119.1	H27B—C27—H27C	109.5
C12—C11—C10	119.5 (6)	O3—C28—N4	135.6 (19)
C12—C11—H11	120.3	O3—C28—H28	112.2
C10—C11—H11	120.3	N4—C28—H28	112.2
O2—Zn1—N1—C7	90.2 (5)	C1—C6—C7—N1	−0.4 (10)
O1—Zn1—N1—C7	−7.2 (5)	C7—N1—C8—C13	−163.0 (5)
N3—Zn1—N1—C7	−102.9 (5)	Zn1—N1—C8—C13	13.6 (6)
N2—Zn1—N1—C7	159.1 (5)	C7—N1—C8—C9	19.3 (9)
O2—Zn1—N1—C8	−86.3 (4)	Zn1—N1—C8—C9	−164.2 (5)
O1—Zn1—N1—C8	176.4 (4)	C13—C8—C9—C10	0.8 (9)
N3—Zn1—N1—C8	80.6 (4)	N1—C8—C9—C10	178.5 (6)
N2—Zn1—N1—C8	−17.4 (4)	C8—C9—C10—C11	−0.7 (11)
O2—Zn1—N2—C14	−13.7 (5)	C9—C10—C11—C12	0.4 (12)
O1—Zn1—N2—C14	−114.9 (6)	C10—C11—C12—C13	−0.2 (11)
N3—Zn1—N2—C14	92.0 (5)	C9—C8—C13—C12	−0.6 (9)
N1—Zn1—N2—C14	−160.5 (5)	N1—C8—C13—C12	−178.4 (5)
O2—Zn1—N2—C13	165.9 (4)	C9—C8—C13—N2	−179.1 (6)
O1—Zn1—N2—C13	64.6 (7)	N1—C8—C13—N2	3.1 (7)
N3—Zn1—N2—C13	−88.5 (4)	C11—C12—C13—C8	0.3 (10)
N1—Zn1—N2—C13	19.1 (4)	C11—C12—C13—N2	178.6 (6)
O2—Zn1—N3—C21	−84.2 (4)	C14—N2—C13—C8	161.6 (5)
O1—Zn1—N3—C21	13.0 (5)	Zn1—N2—C13—C8	−18.0 (6)
N1—Zn1—N3—C21	103.7 (4)	C14—N2—C13—C12	−16.8 (9)
N2—Zn1—N3—C21	−175.7 (4)	Zn1—N2—C13—C12	163.6 (5)
O2—Zn1—N3—C25	96.4 (5)	C13—N2—C14—C15	−174.7 (5)
O1—Zn1—N3—C25	−166.3 (5)	Zn1—N2—C14—C15	4.9 (8)
N1—Zn1—N3—C25	−75.6 (5)	N2—C14—C15—C16	−175.7 (6)
N2—Zn1—N3—C25	4.9 (5)	N2—C14—C15—C20	9.5 (9)
O2—Zn1—O1—C1	−140.6 (5)	C20—C15—C16—C17	2.4 (9)
N3—Zn1—O1—C1	113.0 (5)	C14—C15—C16—C17	−172.5 (6)
N1—Zn1—O1—C1	3.7 (5)	C15—C16—C17—C18	1.5 (10)
N2—Zn1—O1—C1	−40.5 (8)	C15—C16—C17—Br3	−179.6 (5)
O1—Zn1—O2—C20	175.5 (4)	C16—C17—C18—C19	−2.3 (10)
N3—Zn1—O2—C20	−86.9 (5)	Br3—C17—C18—C19	178.8 (4)
N1—Zn1—O2—C20	80.3 (5)	C17—C18—C19—C20	−0.9 (9)
N2—Zn1—O2—C20	14.7 (5)	C17—C18—C19—Br4	177.9 (5)
Zn1—O1—C1—C6	0.7 (8)	Zn1—O2—C20—C19	174.7 (4)
Zn1—O1—C1—C2	−179.6 (4)	Zn1—O2—C20—C15	−6.4 (8)
O1—C1—C2—C3	−175.8 (6)	C18—C19—C20—O2	−176.6 (5)
C6—C1—C2—C3	4.0 (9)	Br4—C19—C20—O2	4.6 (7)
O1—C1—C2—Br1	3.3 (7)	C18—C19—C20—C15	4.4 (8)
C6—C1—C2—Br1	−176.9 (4)	Br4—C19—C20—C15	−174.4 (4)
C1—C2—C3—C4	−2.9 (10)	C16—C15—C20—O2	176.0 (5)
Br1—C2—C3—C4	178.0 (5)	C14—C15—C20—O2	−9.4 (9)
C2—C3—C4—C5	0.4 (9)	C16—C15—C20—C19	−5.1 (8)
C2—C3—C4—Br2	179.1 (5)	C14—C15—C20—C19	169.6 (5)
C3—C4—C5—C6	0.7 (9)	C25—N3—C21—C22	2.1 (9)
Br2—C4—C5—C6	−178.0 (4)	Zn1—N3—C21—C22	−177.3 (5)
C4—C5—C6—C1	0.5 (9)	N3—C21—C22—C23	−2.9 (10)
C4—C5—C6—C7	−178.6 (6)	C21—C22—C23—C24	1.7 (11)
O1—C1—C6—C5	177.1 (5)	C22—C23—C24—C25	0.0 (11)
C2—C1—C6—C5	−2.7 (8)	C21—N3—C25—C24	−0.3 (9)
O1—C1—C6—C7	−3.9 (9)	Zn1—N3—C25—C24	179.1 (5)
C2—C1—C6—C7	176.4 (5)	C23—C24—C25—N3	−0.8 (11)
C8—N1—C7—C6	−177.1 (5)	C27—N4—C28—O3	1 (2)
Zn1—N1—C7—C6	6.8 (9)	C26—N4—C28—O3	177.6 (15)
C5—C6—C7—N1	178.7 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O1	0.93	2.53	3.092 (7)	119
C24—H24···O2^i	0.93	2.56	3.275 (8)	134
C12—H12···O3^ii	0.93	2.48	3.395 (11)	168

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