Bis{4-bromo-2-[tris(hydroxymethyl)methyliminomethyl]phenolato}zinc(II) methanol disolvate

In the title compound, [Zn(C₁₁H₁₃BrNO₄)₂]·2CH₃OH, a distorted trans-ZnN₂O₄ octa­hedron arises from the coordination of the two tridentate ligands. A network of O—H...O hydrogen bonds helps to establish the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](Wave) = 0.000 Å
• R factor = 0.041
• wR factor = 0.099
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.939
            Tmax scaled      0.553 Tmin scaled      0.466

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

(I)

Crystal data

[Zn(C11H13BrNO4)2]·2CH4O	F(000) = 1488
Mr = 735.72	Dx = 1.705 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3406 reflections
a = 10.660 (3) Å	θ = 2.5–26.2°
b = 12.588 (4) Å	µ = 3.70 mm^−1
c = 21.816 (6) Å	T = 294 K
β = 101.766 (5)°	Block, colourless
V = 2865.8 (14) Å^3	0.22 × 0.20 × 0.16 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer	4954 independent reflections
Radiation source: fine-focus sealed tube	3357 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→12
Tmin = 0.496, Tmax = 0.589	k = −14→14
13051 measured reflections	l = −25→12

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)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.099	w = 1/[σ^2(Fo^2) + (0.0383P)^2 + 2.6932P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
4954 reflections	Δρmax = 0.69 e Å^−3
380 parameters	Δρmin = −0.88 e Å^−3
21 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0022 (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	Occ. (<1)
Zn1	0.52106 (4)	0.05358 (4)	0.16421 (2)	0.02535 (16)
Br1	0.51538 (7)	0.42206 (6)	−0.10300 (3)	0.0866 (3)
Br2	0.60959 (7)	0.12275 (5)	0.51135 (3)	0.0717 (2)
O1	0.6199 (3)	0.1743 (2)	0.13661 (13)	0.0328 (7)
O2	0.4455 (3)	0.1270 (2)	0.23134 (14)	0.0374 (8)
O3	0.6233 (3)	−0.0525 (2)	0.10683 (13)	0.0314 (7)
H3	0.6671	−0.0154	0.0828	0.038*
O4	0.9729 (3)	−0.0525 (3)	0.18263 (15)	0.0435 (8)
H4	1.0201	−0.0802	0.2128	0.065*
O5	0.7230 (3)	−0.2308 (3)	0.27119 (15)	0.0409 (8)
H5	0.7532	−0.2635	0.3033	0.061*
O6	0.3989 (3)	−0.0892 (2)	0.16294 (14)	0.0379 (8)
H6	0.4104	−0.1185	0.2013	0.046*
O7	0.0247 (3)	−0.0005 (3)	0.07274 (14)	0.0440 (9)
H7	0.0143	−0.0099	0.1086	0.066*
O8	0.2303 (3)	−0.0289 (3)	−0.02819 (13)	0.0350 (7)
H8	0.1530	−0.0177	−0.0378	0.053*
N1	0.6643 (3)	−0.0126 (3)	0.23217 (15)	0.0234 (8)
N2	0.3671 (3)	0.0811 (3)	0.09071 (15)	0.0239 (8)
C1	0.5926 (4)	0.2266 (3)	0.08394 (19)	0.0270 (10)
C2	0.6857 (4)	0.2942 (4)	0.0670 (2)	0.0362 (11)
H2	0.7651	0.3000	0.0940	0.043*
C3	0.6639 (5)	0.3509 (4)	0.0130 (2)	0.0426 (13)
H3A	0.7280	0.3938	0.0032	0.051*
C4	0.5463 (5)	0.3446 (4)	−0.0272 (2)	0.0406 (12)
C5	0.4527 (5)	0.2804 (3)	−0.0134 (2)	0.0373 (12)
H5A	0.3737	0.2771	−0.0409	0.045*
C6	0.4732 (4)	0.2195 (3)	0.04149 (18)	0.0273 (10)
C7	0.3691 (4)	0.1487 (3)	0.04742 (19)	0.0269 (10)
H7A	0.2956	0.1532	0.0162	0.032*
C8	0.2568 (4)	0.0073 (3)	0.08492 (19)	0.0260 (10)
C9	0.2608 (4)	−0.0730 (3)	0.0329 (2)	0.0318 (11)
H9A	0.3459	−0.1038	0.0395	0.038*
H9B	0.2009	−0.1299	0.0358	0.038*
C10	0.1304 (4)	0.0686 (4)	0.0738 (2)	0.0323 (11)
H10A	0.1332	0.1207	0.1068	0.039*
H10B	0.1193	0.1062	0.0343	0.039*
C11	0.2724 (4)	−0.0518 (4)	0.1472 (2)	0.0325 (11)
H11A	0.2550	−0.0044	0.1795	0.039*
H11B	0.2128	−0.1109	0.1433	0.039*
C12	0.4813 (4)	0.1176 (3)	0.2920 (2)	0.0339 (11)
C13	0.4058 (5)	0.1639 (4)	0.3310 (2)	0.0541 (15)
H13	0.3283	0.1955	0.3128	0.065*
C14	0.4432 (6)	0.1636 (4)	0.3947 (2)	0.0588 (16)
H14	0.3912	0.1947	0.4192	0.071*
C15	0.5572 (6)	0.1177 (4)	0.4228 (2)	0.0452 (13)
C16	0.6309 (5)	0.0685 (3)	0.3874 (2)	0.0374 (12)
H16	0.7068	0.0358	0.4069	0.045*
C17	0.5947 (4)	0.0662 (3)	0.32185 (19)	0.0307 (10)
C18	0.6778 (4)	0.0066 (3)	0.2904 (2)	0.0297 (10)
H18	0.7509	−0.0216	0.3159	0.036*
C19	0.7624 (4)	−0.0779 (3)	0.21007 (18)	0.0250 (10)
C20	0.8699 (4)	−0.0016 (4)	0.2026 (2)	0.0334 (11)
H20A	0.8350	0.0528	0.1724	0.040*
H20B	0.9021	0.0332	0.2424	0.040*
C21	0.8191 (4)	−0.1673 (3)	0.2539 (2)	0.0320 (11)
H21A	0.8730	−0.2113	0.2335	0.038*
H21B	0.8724	−0.1373	0.2913	0.038*
C22	0.6986 (4)	−0.1271 (3)	0.1473 (2)	0.0324 (11)
H22A	0.7643	−0.1554	0.1269	0.039*
H22B	0.6446	−0.1857	0.1548	0.039*
O9	0.4681 (12)	0.8090 (7)	0.2725 (6)	0.054 (3)	0.50
H9	0.5438	0.8062	0.2701	0.081*	0.50
C23	0.4187 (12)	0.7043 (8)	0.2733 (9)	0.068 (4)	0.50
H23A	0.4756	0.6626	0.3038	0.101*	0.50
H23B	0.4114	0.6727	0.2327	0.101*	0.50
H23C	0.3358	0.7070	0.2840	0.101*	0.50
O9'	0.4698 (13)	0.7615 (11)	0.2460 (5)	0.073 (4)	0.50
H9'	0.5513	0.7643	0.2540	0.109*	0.50
C23'	0.4472 (15)	0.7556 (17)	0.3074 (5)	0.087 (5)	0.50
H23D	0.4963	0.6984	0.3295	0.130*	0.50
H23E	0.3577	0.7432	0.3057	0.130*	0.50
H23F	0.4721	0.8213	0.3288	0.130*	0.50
O10	0.1303 (4)	0.8379 (3)	0.27540 (16)	0.0559 (10)
H10	0.1046	0.7774	0.2791	0.084*
C24	0.1865 (7)	0.8772 (5)	0.3336 (3)	0.101 (3)
H24A	0.2160	0.9484	0.3293	0.151*
H24B	0.2578	0.8331	0.3519	0.151*
H24C	0.1248	0.8775	0.3601	0.151*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0212 (3)	0.0275 (3)	0.0258 (3)	−0.0008 (2)	0.0014 (2)	0.0042 (2)
Br1	0.0930 (5)	0.0989 (6)	0.0644 (4)	−0.0313 (4)	0.0078 (4)	0.0485 (4)
Br2	0.1147 (6)	0.0710 (4)	0.0301 (3)	−0.0070 (4)	0.0160 (3)	−0.0116 (3)
O1	0.0321 (18)	0.0323 (17)	0.0312 (17)	−0.0097 (14)	0.0001 (14)	0.0019 (14)
O2	0.0369 (19)	0.0443 (19)	0.0315 (17)	0.0124 (15)	0.0084 (15)	0.0043 (15)
O3	0.0302 (17)	0.0364 (17)	0.0279 (16)	0.0000 (15)	0.0063 (13)	0.0039 (14)
O4	0.0291 (19)	0.060 (2)	0.0449 (19)	0.0109 (17)	0.0163 (16)	0.0171 (18)
O5	0.0318 (19)	0.045 (2)	0.044 (2)	0.0018 (16)	0.0031 (15)	0.0217 (16)
O6	0.0280 (18)	0.0426 (19)	0.0407 (18)	−0.0019 (15)	0.0013 (15)	0.0216 (15)
O7	0.0206 (18)	0.076 (2)	0.0351 (18)	−0.0106 (17)	0.0058 (15)	0.0099 (18)
O8	0.0247 (17)	0.051 (2)	0.0293 (17)	−0.0010 (16)	0.0049 (13)	0.0012 (15)
N1	0.0187 (19)	0.0242 (18)	0.027 (2)	0.0015 (15)	0.0033 (15)	0.0012 (16)
N2	0.0185 (19)	0.029 (2)	0.0240 (18)	−0.0007 (15)	0.0031 (15)	0.0029 (16)
C1	0.035 (3)	0.019 (2)	0.028 (2)	−0.0042 (19)	0.009 (2)	−0.0057 (19)
C2	0.033 (3)	0.035 (3)	0.039 (3)	−0.013 (2)	0.003 (2)	−0.002 (2)
C3	0.051 (3)	0.035 (3)	0.046 (3)	−0.021 (2)	0.017 (3)	0.001 (2)
C4	0.051 (3)	0.039 (3)	0.033 (3)	−0.015 (2)	0.010 (2)	0.007 (2)
C5	0.042 (3)	0.037 (3)	0.031 (3)	−0.009 (2)	0.003 (2)	0.004 (2)
C6	0.033 (3)	0.026 (2)	0.025 (2)	−0.003 (2)	0.008 (2)	−0.0018 (19)
C7	0.023 (2)	0.031 (2)	0.024 (2)	−0.0028 (19)	0.0008 (18)	0.002 (2)
C8	0.017 (2)	0.033 (2)	0.028 (2)	−0.0060 (19)	0.0039 (18)	0.003 (2)
C9	0.027 (3)	0.029 (2)	0.040 (3)	−0.005 (2)	0.007 (2)	0.003 (2)
C10	0.021 (2)	0.043 (3)	0.033 (2)	0.001 (2)	0.0062 (19)	0.003 (2)
C11	0.021 (2)	0.041 (3)	0.035 (3)	−0.007 (2)	0.0051 (19)	0.010 (2)
C12	0.039 (3)	0.028 (2)	0.036 (3)	0.001 (2)	0.012 (2)	0.003 (2)
C13	0.066 (4)	0.058 (3)	0.044 (3)	0.028 (3)	0.023 (3)	0.009 (3)
C14	0.083 (4)	0.060 (4)	0.043 (3)	0.021 (3)	0.036 (3)	0.005 (3)
C15	0.074 (4)	0.040 (3)	0.023 (2)	−0.005 (3)	0.012 (3)	0.001 (2)
C16	0.050 (3)	0.033 (3)	0.027 (2)	0.003 (2)	0.004 (2)	−0.001 (2)
C17	0.037 (3)	0.028 (2)	0.028 (2)	−0.003 (2)	0.006 (2)	0.001 (2)
C18	0.027 (3)	0.031 (2)	0.028 (2)	0.001 (2)	−0.0033 (19)	0.003 (2)
C19	0.019 (2)	0.030 (2)	0.026 (2)	0.0025 (18)	0.0050 (18)	0.0036 (19)
C20	0.026 (3)	0.042 (3)	0.032 (3)	−0.001 (2)	0.007 (2)	0.004 (2)
C21	0.023 (3)	0.038 (3)	0.036 (3)	0.006 (2)	0.006 (2)	0.009 (2)
C22	0.035 (3)	0.027 (2)	0.036 (3)	0.003 (2)	0.008 (2)	0.002 (2)
O9	0.041 (5)	0.067 (7)	0.057 (7)	0.013 (5)	0.018 (6)	0.029 (5)
C23	0.050 (7)	0.064 (7)	0.092 (8)	0.015 (6)	0.021 (7)	0.012 (7)
O9'	0.038 (6)	0.107 (10)	0.073 (9)	0.011 (7)	0.008 (6)	0.053 (7)
C23'	0.066 (8)	0.112 (9)	0.086 (8)	0.008 (7)	0.024 (7)	0.021 (8)
O10	0.047 (2)	0.054 (2)	0.060 (2)	−0.0024 (19)	−0.0043 (19)	0.004 (2)
C24	0.118 (6)	0.080 (4)	0.094 (5)	0.025 (4)	−0.005 (4)	−0.042 (4)

Geometric parameters (Å, º)

Zn1—O1	2.010 (3)	C9—H9B	0.9700
Zn1—O2	2.032 (3)	C10—H10A	0.9700
Zn1—N1	2.074 (3)	C10—H10B	0.9700
Zn1—N2	2.076 (3)	C11—H11A	0.9700
Zn1—O6	2.216 (3)	C11—H11B	0.9700
Zn1—O3	2.257 (3)	C12—C17	1.408 (6)
Br1—C4	1.889 (4)	C12—C13	1.412 (6)
Br2—C15	1.899 (5)	C13—C14	1.365 (7)
O1—C1	1.305 (5)	C13—H13	0.9300
O2—C12	1.306 (5)	C14—C15	1.373 (7)
O3—C22	1.420 (5)	C14—H14	0.9300
O3—H3	0.8999	C15—C16	1.358 (6)
O4—C20	1.415 (5)	C16—C17	1.403 (6)
O4—H4	0.8200	C16—H16	0.9300
O5—C21	1.410 (5)	C17—C18	1.437 (6)
O5—H5	0.8200	C18—H18	0.9300
O6—C11	1.403 (5)	C19—C21	1.520 (6)
O6—H6	0.9002	C19—C20	1.528 (6)
O7—C10	1.419 (5)	C19—C22	1.531 (6)
O7—H7	0.8200	C20—H20A	0.9700
O8—C9	1.420 (5)	C20—H20B	0.9700
O8—H8	0.8200	C21—H21A	0.9700
N1—C18	1.272 (5)	C21—H21B	0.9700
N1—C19	1.486 (5)	C22—H22A	0.9700
N2—C7	1.275 (5)	C22—H22B	0.9700
N2—C8	1.483 (5)	O9—C23	1.421 (9)
C1—C2	1.412 (6)	O9—H9	0.8200
C1—C6	1.416 (6)	O9—H9'	1.1878
C2—C3	1.356 (6)	C23—H23A	0.9600
C2—H2	0.9300	C23—H23B	0.9600
C3—C4	1.379 (7)	C23—H23C	0.9600
C3—H3A	0.9300	O9'—C23'	1.412 (9)
C4—C5	1.365 (6)	O9'—H9'	0.8505
C5—C6	1.401 (6)	C23'—H23D	0.9600
C5—H5A	0.9300	C23'—H23E	0.9600
C6—C7	1.448 (6)	C23'—H23F	0.9600
C7—H7A	0.9300	O10—C24	1.381 (6)
C8—C9	1.525 (6)	O10—H10	0.8200
C8—C11	1.528 (6)	C24—H24A	0.9600
C8—C10	1.529 (6)	C24—H24B	0.9600
C9—H9A	0.9700	C24—H24C	0.9600
O1—Zn1—O2	100.45 (12)	C8—C10—H10B	109.4
O1—Zn1—N1	99.42 (12)	H10A—C10—H10B	108.0
O2—Zn1—N1	90.56 (12)	O6—C11—C8	107.8 (3)
O1—Zn1—N2	91.30 (12)	O6—C11—H11A	110.1
O2—Zn1—N2	96.53 (12)	C8—C11—H11A	110.1
N1—Zn1—N2	165.89 (13)	O6—C11—H11B	110.1
O1—Zn1—O6	162.14 (11)	C8—C11—H11B	110.1
O2—Zn1—O6	93.40 (12)	H11A—C11—H11B	108.5
N1—Zn1—O6	91.60 (12)	O2—C12—C17	123.8 (4)
N2—Zn1—O6	75.85 (12)	O2—C12—C13	119.3 (4)
O1—Zn1—O3	86.50 (11)	C17—C12—C13	116.8 (4)
O2—Zn1—O3	167.43 (11)	C14—C13—C12	122.0 (5)
N1—Zn1—O3	77.90 (12)	C14—C13—H13	119.0
N2—Zn1—O3	93.74 (11)	C12—C13—H13	119.0
O6—Zn1—O3	82.10 (11)	C13—C14—C15	120.3 (5)
C1—O1—Zn1	127.5 (3)	C13—C14—H14	119.9
C12—O2—Zn1	127.7 (3)	C15—C14—H14	119.9
C22—O3—Zn1	108.8 (2)	C16—C15—C14	120.0 (4)
C22—O3—H3	114.3	C16—C15—Br2	120.7 (4)
Zn1—O3—H3	112.5	C14—C15—Br2	119.4 (4)
C20—O4—H4	109.5	C15—C16—C17	121.3 (4)
C21—O5—H5	109.5	C15—C16—H16	119.4
C11—O6—Zn1	105.3 (2)	C17—C16—H16	119.4
C11—O6—H6	107.9	C16—C17—C12	119.6 (4)
Zn1—O6—H6	110.6	C16—C17—C18	115.4 (4)
C10—O7—H7	109.5	C12—C17—C18	125.0 (4)
C9—O8—H8	109.5	N1—C18—C17	128.3 (4)
C18—N1—C19	119.0 (3)	N1—C18—H18	115.8
C18—N1—Zn1	123.7 (3)	C17—C18—H18	115.8
C19—N1—Zn1	117.0 (2)	N1—C19—C21	114.9 (3)
C7—N2—C8	119.2 (3)	N1—C19—C20	106.3 (3)
C7—N2—Zn1	123.6 (3)	C21—C19—C20	108.8 (3)
C8—N2—Zn1	116.7 (2)	N1—C19—C22	107.5 (3)
O1—C1—C2	119.5 (4)	C21—C19—C22	108.1 (3)
O1—C1—C6	123.6 (4)	C20—C19—C22	111.4 (3)
C2—C1—C6	117.0 (4)	O4—C20—C19	113.2 (4)
C3—C2—C1	122.6 (4)	O4—C20—H20A	108.9
C3—C2—H2	118.7	C19—C20—H20A	108.9
C1—C2—H2	118.7	O4—C20—H20B	108.9
C2—C3—C4	119.7 (4)	C19—C20—H20B	108.9
C2—C3—H3A	120.1	H20A—C20—H20B	107.8
C4—C3—H3A	120.1	O5—C21—C19	111.8 (3)
C5—C4—C3	120.2 (4)	O5—C21—H21A	109.3
C5—C4—Br1	119.6 (4)	C19—C21—H21A	109.3
C3—C4—Br1	120.1 (3)	O5—C21—H21B	109.3
C4—C5—C6	121.3 (4)	C19—C21—H21B	109.3
C4—C5—H5A	119.3	H21A—C21—H21B	107.9
C6—C5—H5A	119.3	O3—C22—C19	112.3 (3)
C5—C6—C1	119.1 (4)	O3—C22—H22A	109.1
C5—C6—C7	115.1 (4)	C19—C22—H22A	109.1
C1—C6—C7	125.7 (4)	O3—C22—H22B	109.1
N2—C7—C6	127.3 (4)	C19—C22—H22B	109.1
N2—C7—H7A	116.4	H22A—C22—H22B	107.9
C6—C7—H7A	116.4	C23—O9—H9'	82.4
N2—C8—C9	109.7 (3)	H9—O9—H9'	31.3
N2—C8—C11	106.8 (3)	C23'—O9'—H9'	99.8
C9—C8—C11	108.9 (4)	O9'—C23'—H23D	109.5
N2—C8—C10	110.8 (3)	O9'—C23'—H23E	109.5
C9—C8—C10	111.9 (3)	H23D—C23'—H23E	109.5
C11—C8—C10	108.6 (3)	O9'—C23'—H23F	109.5
O8—C9—C8	113.8 (3)	H23D—C23'—H23F	109.5
O8—C9—H9A	108.8	H23E—C23'—H23F	109.5
C8—C9—H9A	108.8	C24—O10—H10	109.5
O8—C9—H9B	108.8	O10—C24—H24A	109.5
C8—C9—H9B	108.8	O10—C24—H24B	109.5
H9A—C9—H9B	107.7	H24A—C24—H24B	109.5
O7—C10—C8	111.4 (4)	O10—C24—H24C	109.5
O7—C10—H10A	109.4	H24A—C24—H24C	109.5
C8—C10—H10A	109.4	H24B—C24—H24C	109.5
O7—C10—H10B	109.4
O2—Zn1—O1—C1	−108.3 (3)	C8—N2—C7—C6	−173.2 (4)
N1—Zn1—O1—C1	159.4 (3)	Zn1—N2—C7—C6	−1.7 (6)
N2—Zn1—O1—C1	−11.4 (3)	C5—C6—C7—N2	175.6 (4)
O6—Zn1—O1—C1	32.0 (6)	C1—C6—C7—N2	−0.7 (7)
O3—Zn1—O1—C1	82.3 (3)	C7—N2—C8—C9	70.1 (5)
O1—Zn1—O2—C12	−104.7 (4)	Zn1—N2—C8—C9	−102.0 (3)
N1—Zn1—O2—C12	−5.0 (4)	C7—N2—C8—C11	−172.0 (4)
N2—Zn1—O2—C12	162.7 (4)	Zn1—N2—C8—C11	15.8 (4)
O6—Zn1—O2—C12	86.6 (4)	C7—N2—C8—C10	−54.0 (5)
O3—Zn1—O2—C12	18.1 (8)	Zn1—N2—C8—C10	133.9 (3)
O1—Zn1—O3—C22	117.9 (3)	N2—C8—C9—O8	−71.4 (4)
O2—Zn1—O3—C22	−6.3 (7)	C11—C8—C9—O8	172.1 (3)
N1—Zn1—O3—C22	17.5 (2)	C10—C8—C9—O8	52.0 (5)
N2—Zn1—O3—C22	−151.1 (3)	N2—C8—C10—O7	−175.7 (3)
O6—Zn1—O3—C22	−75.9 (3)	C9—C8—C10—O7	61.5 (4)
O1—Zn1—O6—C11	−81.8 (5)	C11—C8—C10—O7	−58.7 (5)
O2—Zn1—O6—C11	59.1 (3)	Zn1—O6—C11—C8	56.4 (4)
N1—Zn1—O6—C11	149.8 (3)	N2—C8—C11—O6	−48.4 (4)
N2—Zn1—O6—C11	−36.7 (2)	C9—C8—C11—O6	69.9 (4)
O3—Zn1—O6—C11	−132.7 (3)	C10—C8—C11—O6	−168.0 (3)
O1—Zn1—N1—C18	97.3 (3)	Zn1—O2—C12—C17	10.7 (6)
O2—Zn1—N1—C18	−3.3 (3)	Zn1—O2—C12—C13	−171.4 (3)
N2—Zn1—N1—C18	−123.7 (5)	O2—C12—C13—C14	−175.0 (5)
O6—Zn1—N1—C18	−96.8 (3)	C17—C12—C13—C14	3.1 (8)
O3—Zn1—N1—C18	−178.3 (3)	C12—C13—C14—C15	0.1 (9)
O1—Zn1—N1—C19	−76.8 (3)	C13—C14—C15—C16	−2.6 (8)
O2—Zn1—N1—C19	−177.5 (3)	C13—C14—C15—Br2	177.8 (4)
N2—Zn1—N1—C19	62.2 (6)	C14—C15—C16—C17	1.9 (7)
O6—Zn1—N1—C19	89.1 (3)	Br2—C15—C16—C17	−178.6 (3)
O3—Zn1—N1—C19	7.5 (2)	C15—C16—C17—C12	1.4 (7)
O1—Zn1—N2—C7	5.9 (3)	C15—C16—C17—C18	−176.7 (4)
O2—Zn1—N2—C7	106.6 (3)	O2—C12—C17—C16	174.3 (4)
N1—Zn1—N2—C7	−133.7 (5)	C13—C12—C17—C16	−3.7 (6)
O6—Zn1—N2—C7	−161.5 (3)	O2—C12—C17—C18	−7.8 (7)
O3—Zn1—N2—C7	−80.7 (3)	C13—C12—C17—C18	174.2 (4)
O1—Zn1—N2—C8	177.7 (3)	C19—N1—C18—C17	−179.2 (4)
O2—Zn1—N2—C8	−81.7 (3)	Zn1—N1—C18—C17	6.7 (6)
N1—Zn1—N2—C8	38.1 (6)	C16—C17—C18—N1	176.3 (4)
O6—Zn1—N2—C8	10.2 (3)	C12—C17—C18—N1	−1.7 (7)
O3—Zn1—N2—C8	91.1 (3)	C18—N1—C19—C21	36.1 (5)
Zn1—O1—C1—C2	−167.2 (3)	Zn1—N1—C19—C21	−149.5 (3)
Zn1—O1—C1—C6	12.4 (6)	C18—N1—C19—C20	−84.3 (4)
O1—C1—C2—C3	180.0 (4)	Zn1—N1—C19—C20	90.2 (3)
C6—C1—C2—C3	0.3 (6)	C18—N1—C19—C22	156.4 (4)
C1—C2—C3—C4	0.9 (7)	Zn1—N1—C19—C22	−29.2 (4)
C2—C3—C4—C5	−1.0 (7)	N1—C19—C20—O4	179.0 (3)
C2—C3—C4—Br1	−179.3 (4)	C21—C19—C20—O4	54.8 (5)
C3—C4—C5—C6	−0.1 (7)	C22—C19—C20—O4	−64.3 (4)
Br1—C4—C5—C6	178.2 (3)	N1—C19—C21—O5	51.2 (5)
C4—C5—C6—C1	1.4 (7)	C20—C19—C21—O5	170.2 (3)
C4—C5—C6—C7	−175.2 (4)	C22—C19—C21—O5	−68.7 (4)
O1—C1—C6—C5	178.9 (4)	Zn1—O3—C22—C19	−38.9 (4)
C2—C1—C6—C5	−1.5 (6)	N1—C19—C22—O3	45.0 (4)
O1—C1—C6—C7	−4.9 (6)	C21—C19—C22—O3	169.5 (3)
C2—C1—C6—C7	174.7 (4)	C20—C19—C22—O3	−71.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O10^i	0.82	1.91	2.726 (5)	172
O5—H5···O1^ii	0.82	1.85	2.627 (4)	157
O7—H7···O4^iii	0.82	1.84	2.650 (4)	169
O8—H8···O7^iv	0.82	1.91	2.719 (4)	171
O9—H9···O5^v	0.82	1.96	2.768 (13)	168
O9′—H9′···O5^v	0.85	1.79	2.643 (14)	180
O10—H10···O2^vi	0.82	1.97	2.771 (5)	166

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