Bis[N-(5,7-dibromo­quinolin-8-yl)-3,5-bis­(trifluoro­meth­yl)benzene­sulfonamidato-κ²N,N′]zinc(II)

In the title compound, [Zn(C₁₇H₇Br₂F₆N₂O₂S)₂], the zinc(II) ion has a distorted tetra­hedral geometry formed by the N atoms of the quinoline and the sulfonamide groups. One inter­molecular C—H...O hydrogen bond to a sulfonyl O atom is observed.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.042
• wR factor = 0.100
• Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT213_ALERT_2_B Atom F4      has ADP max/min Ratio .............       4.10 prola
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C17
PLAT431_ALERT_2_B Short Inter HL..A Contact  Br2    ..  O3      ..       2.92 Ang.

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT213_ALERT_2_C Atom F6      has ADP max/min Ratio .............       3.50 prola
PLAT213_ALERT_2_C Atom F8      has ADP max/min Ratio .............       3.60 prola
PLAT213_ALERT_2_C Atom F11     has ADP max/min Ratio .............       3.20 prola
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.94 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    F     Ueq(max)/Ueq(min) ...       2.78 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C33
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  F11     ..       3.23 Ang.

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  10 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: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2004); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Bis[N-(5,7-dibromoquinolin-8-yl)-3,5-bis(trifluoromethyl)benzenesulfonamidato- κ²N,N']zinc(II)

Crystal data

[Zn(C17H7Br2F6N2O2S)2]	Z = 2
Mr = 1219.62	F(000) = 1176
Triclinic, P1	Dx = 2.038 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.7057 (6) Å	Cell parameters from 7161 reflections
b = 12.4768 (6) Å	θ = 1.9–27.6°
c = 14.0759 (7) Å	µ = 4.85 mm^−1
α = 90.091 (4)°	T = 100 K
β = 100.293 (4)°	Prism, colourless
γ = 100.519 (4)°	0.55 × 0.30 × 0.25 mm
V = 1987.46 (17) Å^3

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	7836 independent reflections
Radiation source: fine-focus sealed tube	6792 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω and φ scans	θmax = 26.4°, θmin = 4.1°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2004)	h = −14→14
Tmin = 0.176, Tmax = 0.377	k = −15→15
13514 measured reflections	l = −17→14

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.100	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0338P)^2 + 9.6563P] where P = (Fo^2 + 2Fc^2)/3
7836 reflections	(Δ/σ)max = 0.001
550 parameters	Δρmax = 1.70 e Å^−3
0 restraints	Δρmin = −1.14 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
Br1	0.63256 (4)	0.65420 (4)	0.30364 (3)	0.02872 (12)
Br2	0.69503 (4)	0.52909 (4)	−0.05887 (5)	0.04139 (15)
Br3	−0.03453 (4)	0.80449 (4)	0.29892 (3)	0.02587 (11)
Br4	−0.05249 (4)	1.21431 (4)	0.14122 (4)	0.02835 (12)
Zn1	0.31545 (4)	0.83653 (4)	0.09990 (3)	0.01546 (11)
S1	0.53538 (9)	0.90952 (8)	0.24087 (7)	0.0166 (2)
S2	0.11487 (9)	0.69101 (8)	0.13424 (7)	0.0161 (2)
F1	0.2315 (3)	0.7669 (4)	0.4620 (2)	0.0661 (13)
F2	0.3317 (3)	0.6936 (3)	0.5761 (3)	0.0469 (8)
F3	0.3058 (3)	0.8544 (3)	0.5965 (3)	0.0519 (9)
F4	0.7548 (4)	0.8656 (6)	0.6813 (3)	0.107 (2)
F5	0.8342 (4)	0.8286 (5)	0.5666 (4)	0.1011 (19)
F6	0.8256 (4)	0.9861 (4)	0.5933 (4)	0.108 (2)
F7	−0.1822 (3)	0.3905 (3)	0.2762 (3)	0.0556 (10)
F8	−0.0874 (3)	0.3218 (3)	0.3942 (4)	0.0769 (15)
F9	−0.1321 (3)	0.4783 (3)	0.4100 (3)	0.0597 (11)
F10	0.3983 (3)	0.4256 (3)	0.3396 (2)	0.0490 (9)
F11	0.3329 (3)	0.4090 (3)	0.4716 (3)	0.0562 (11)
F12	0.4210 (2)	0.5648 (2)	0.4332 (2)	0.0388 (7)
O1	0.4619 (3)	0.9914 (2)	0.2214 (2)	0.0234 (6)
O2	0.6552 (3)	0.9355 (3)	0.2243 (2)	0.0230 (6)
O3	0.1978 (3)	0.6626 (2)	0.0763 (2)	0.0223 (6)
O4	−0.0071 (3)	0.6806 (2)	0.0898 (2)	0.0204 (6)
N1	0.4619 (3)	0.8010 (3)	0.1827 (2)	0.0155 (7)
N2	0.4021 (3)	0.7950 (3)	−0.0101 (2)	0.0187 (7)
N3	0.1763 (3)	0.8095 (3)	0.1775 (3)	0.0162 (7)
N4	0.2397 (3)	0.9669 (3)	0.0579 (2)	0.0145 (7)
C1	0.5175 (3)	0.7360 (3)	0.1311 (3)	0.0164 (8)
C2	0.5943 (4)	0.6697 (3)	0.1691 (3)	0.0194 (8)
C3	0.6457 (4)	0.6078 (4)	0.1112 (4)	0.0268 (10)
H3	0.6993	0.5634	0.1403	0.032*
C4	0.6187 (4)	0.6115 (3)	0.0138 (4)	0.0242 (10)
C5	0.5367 (4)	0.6738 (3)	−0.0323 (3)	0.0219 (9)
C6	0.5036 (4)	0.6814 (4)	−0.1328 (4)	0.0301 (11)
H6	0.5365	0.6422	−0.1757	0.036*
C7	0.4242 (4)	0.7451 (5)	−0.1685 (3)	0.0328 (11)
H7	0.4034	0.7524	−0.2362	0.039*
C8	0.3735 (4)	0.7998 (4)	−0.1051 (3)	0.0258 (10)
H8	0.3163	0.8420	−0.1311	0.031*
C9	0.4856 (3)	0.7355 (3)	0.0281 (3)	0.0171 (8)
C10	0.5402 (4)	0.8830 (3)	0.3654 (3)	0.0180 (8)
C11	0.4345 (4)	0.8505 (3)	0.3974 (3)	0.0206 (9)
H11	0.3613	0.8432	0.3538	0.025*
C12	0.4371 (4)	0.8289 (4)	0.4939 (3)	0.0255 (10)
C13	0.5432 (4)	0.8425 (4)	0.5584 (3)	0.0283 (10)
H13	0.5443	0.8295	0.6250	0.034*
C14	0.6476 (4)	0.8754 (4)	0.5247 (3)	0.0292 (10)
C15	0.6474 (4)	0.8959 (4)	0.4277 (3)	0.0247 (9)
H15	0.7194	0.9183	0.4049	0.030*
C16	0.3265 (5)	0.7875 (4)	0.5309 (3)	0.0329 (11)
C17	0.7639 (5)	0.8890 (5)	0.5928 (4)	0.0421 (14)
C18	0.1138 (3)	0.8959 (3)	0.1684 (3)	0.0155 (8)
C19	0.0236 (4)	0.9108 (3)	0.2160 (3)	0.0180 (8)
C20	−0.0273 (4)	1.0050 (3)	0.2066 (3)	0.0204 (9)
H20	−0.0891	1.0123	0.2402	0.024*
C21	0.0125 (4)	1.0853 (3)	0.1492 (3)	0.0197 (8)
C22	0.1023 (3)	1.0766 (3)	0.0954 (3)	0.0151 (8)
C23	0.1406 (4)	1.1531 (3)	0.0283 (3)	0.0184 (8)
H23	0.1094	1.2183	0.0194	0.022*
C24	0.2232 (4)	1.1324 (3)	−0.0235 (3)	0.0208 (9)
H24	0.2464	1.1807	−0.0716	0.025*
C25	0.2726 (4)	1.0400 (3)	−0.0047 (3)	0.0187 (8)
H25	0.3329	1.0285	−0.0385	0.022*
C26	0.1526 (3)	0.9813 (3)	0.1073 (3)	0.0142 (8)
C27	0.1215 (4)	0.5977 (3)	0.2297 (3)	0.0159 (8)
C28	0.0152 (4)	0.5440 (3)	0.2521 (3)	0.0207 (9)
H28	−0.0580	0.5586	0.2186	0.025*
C29	0.0184 (4)	0.4688 (3)	0.3241 (3)	0.0211 (9)
C30	0.1252 (4)	0.4457 (3)	0.3717 (3)	0.0219 (9)
H30	0.1264	0.3931	0.4205	0.026*
C31	0.2296 (4)	0.4994 (3)	0.3480 (3)	0.0195 (8)
C32	0.2287 (4)	0.5767 (3)	0.2774 (3)	0.0191 (8)
H32	0.3007	0.6148	0.2620	0.023*
C33	−0.0950 (4)	0.4142 (4)	0.3525 (4)	0.0277 (10)
C34	0.3451 (4)	0.4749 (4)	0.3982 (3)	0.0266 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0258 (2)	0.0317 (2)	0.0297 (3)	0.01040 (19)	0.00245 (18)	0.01374 (19)
Br2	0.0279 (3)	0.0305 (3)	0.0689 (4)	0.0026 (2)	0.0201 (2)	−0.0248 (3)
Br3	0.0270 (2)	0.0244 (2)	0.0296 (2)	0.00364 (18)	0.01531 (19)	0.00659 (18)
Br4	0.0289 (2)	0.0207 (2)	0.0380 (3)	0.01330 (18)	0.0043 (2)	−0.00202 (18)
Zn1	0.0144 (2)	0.0178 (2)	0.0159 (2)	0.00577 (18)	0.00455 (17)	0.00366 (17)
S1	0.0178 (5)	0.0179 (5)	0.0138 (5)	0.0012 (4)	0.0040 (4)	0.0017 (4)
S2	0.0161 (5)	0.0138 (5)	0.0190 (5)	0.0045 (4)	0.0034 (4)	0.0041 (4)
F1	0.0291 (17)	0.126 (4)	0.0327 (18)	−0.016 (2)	0.0095 (14)	0.021 (2)
F2	0.053 (2)	0.0339 (17)	0.059 (2)	0.0008 (15)	0.0323 (17)	0.0160 (15)
F3	0.060 (2)	0.0405 (18)	0.063 (2)	0.0011 (16)	0.0414 (19)	−0.0054 (16)
F4	0.050 (2)	0.209 (6)	0.032 (2)	−0.027 (3)	−0.0198 (18)	0.042 (3)
F5	0.054 (3)	0.146 (5)	0.093 (4)	0.042 (3)	−0.036 (3)	−0.021 (3)
F6	0.088 (3)	0.088 (3)	0.093 (4)	−0.049 (3)	−0.061 (3)	0.035 (3)
F7	0.0309 (17)	0.075 (3)	0.050 (2)	−0.0217 (17)	0.0093 (15)	0.0033 (18)
F8	0.043 (2)	0.064 (3)	0.137 (4)	0.0149 (19)	0.047 (2)	0.070 (3)
F9	0.0438 (19)	0.063 (2)	0.074 (3)	−0.0120 (17)	0.0395 (19)	−0.026 (2)
F10	0.0403 (18)	0.063 (2)	0.050 (2)	0.0360 (17)	−0.0031 (15)	−0.0040 (17)
F11	0.0319 (16)	0.076 (3)	0.055 (2)	0.0056 (17)	−0.0033 (15)	0.051 (2)
F12	0.0256 (14)	0.0374 (17)	0.0481 (19)	0.0041 (13)	−0.0053 (13)	0.0041 (14)
O1	0.0318 (17)	0.0184 (15)	0.0206 (16)	0.0062 (13)	0.0049 (13)	0.0018 (12)
O2	0.0212 (15)	0.0273 (16)	0.0192 (15)	−0.0019 (13)	0.0070 (12)	0.0013 (12)
O3	0.0294 (16)	0.0186 (15)	0.0226 (16)	0.0076 (13)	0.0112 (13)	0.0028 (12)
O4	0.0179 (14)	0.0172 (14)	0.0247 (16)	0.0052 (12)	−0.0022 (12)	0.0061 (12)
N1	0.0123 (15)	0.0143 (16)	0.0189 (17)	0.0016 (13)	0.0010 (13)	−0.0010 (13)
N2	0.0162 (16)	0.0232 (18)	0.0169 (17)	0.0025 (14)	0.0050 (14)	−0.0005 (14)
N3	0.0144 (16)	0.0129 (16)	0.0223 (18)	0.0044 (13)	0.0038 (14)	0.0053 (13)
N4	0.0118 (15)	0.0184 (17)	0.0122 (16)	0.0023 (13)	0.0001 (12)	0.0027 (13)
C1	0.0130 (18)	0.0149 (19)	0.020 (2)	−0.0012 (15)	0.0043 (16)	0.0000 (15)
C2	0.0171 (19)	0.0157 (19)	0.025 (2)	0.0025 (16)	0.0028 (17)	0.0054 (16)
C3	0.019 (2)	0.017 (2)	0.046 (3)	0.0056 (17)	0.009 (2)	0.002 (2)
C4	0.017 (2)	0.015 (2)	0.043 (3)	−0.0018 (16)	0.0148 (19)	−0.0083 (18)
C5	0.018 (2)	0.017 (2)	0.030 (2)	−0.0057 (16)	0.0108 (18)	−0.0081 (17)
C6	0.025 (2)	0.034 (3)	0.031 (3)	−0.004 (2)	0.013 (2)	−0.014 (2)
C7	0.027 (2)	0.048 (3)	0.019 (2)	−0.004 (2)	0.0061 (19)	−0.006 (2)
C8	0.023 (2)	0.036 (3)	0.017 (2)	0.0014 (19)	0.0041 (17)	0.0015 (18)
C9	0.0141 (18)	0.0139 (18)	0.023 (2)	−0.0015 (15)	0.0060 (16)	−0.0030 (16)
C10	0.028 (2)	0.0135 (19)	0.0124 (19)	0.0025 (17)	0.0049 (16)	0.0006 (15)
C11	0.021 (2)	0.022 (2)	0.017 (2)	0.0008 (17)	0.0026 (17)	−0.0005 (16)
C12	0.031 (2)	0.024 (2)	0.020 (2)	−0.0001 (19)	0.0068 (19)	0.0022 (18)
C13	0.037 (3)	0.026 (2)	0.017 (2)	−0.003 (2)	0.0035 (19)	0.0030 (18)
C14	0.030 (2)	0.030 (2)	0.022 (2)	−0.002 (2)	−0.0021 (19)	0.0019 (19)
C15	0.023 (2)	0.024 (2)	0.024 (2)	−0.0018 (18)	0.0031 (18)	0.0017 (18)
C16	0.034 (3)	0.043 (3)	0.019 (2)	−0.006 (2)	0.011 (2)	0.003 (2)
C17	0.032 (3)	0.052 (4)	0.031 (3)	−0.008 (3)	−0.005 (2)	0.009 (2)
C18	0.0152 (18)	0.0141 (19)	0.0164 (19)	0.0033 (15)	0.0006 (15)	0.0026 (15)
C19	0.0186 (19)	0.0166 (19)	0.017 (2)	−0.0009 (16)	0.0025 (16)	0.0001 (16)
C20	0.0156 (19)	0.022 (2)	0.024 (2)	0.0037 (16)	0.0037 (16)	−0.0037 (17)
C21	0.0156 (19)	0.020 (2)	0.023 (2)	0.0066 (16)	0.0002 (16)	−0.0039 (17)
C22	0.0125 (18)	0.0138 (19)	0.0162 (19)	0.0023 (15)	−0.0044 (15)	−0.0009 (15)
C23	0.0168 (19)	0.0149 (19)	0.020 (2)	0.0033 (16)	−0.0054 (16)	−0.0004 (16)
C24	0.023 (2)	0.016 (2)	0.021 (2)	0.0019 (17)	0.0009 (17)	0.0072 (16)
C25	0.0166 (19)	0.020 (2)	0.019 (2)	0.0014 (16)	0.0040 (16)	0.0019 (16)
C26	0.0127 (17)	0.0134 (18)	0.0147 (19)	0.0006 (15)	−0.0001 (15)	−0.0042 (15)
C27	0.020 (2)	0.0084 (17)	0.019 (2)	0.0022 (15)	0.0027 (16)	0.0037 (15)
C28	0.022 (2)	0.015 (2)	0.025 (2)	0.0050 (17)	0.0037 (17)	0.0029 (17)
C29	0.021 (2)	0.016 (2)	0.026 (2)	0.0007 (17)	0.0075 (18)	0.0032 (17)
C30	0.028 (2)	0.017 (2)	0.023 (2)	0.0066 (17)	0.0083 (18)	0.0080 (17)
C31	0.022 (2)	0.022 (2)	0.016 (2)	0.0068 (17)	0.0024 (16)	0.0041 (16)
C32	0.019 (2)	0.017 (2)	0.021 (2)	0.0026 (16)	0.0035 (17)	0.0023 (16)
C33	0.024 (2)	0.025 (2)	0.037 (3)	0.0071 (19)	0.013 (2)	0.010 (2)
C34	0.022 (2)	0.030 (2)	0.026 (2)	0.0039 (19)	−0.0007 (18)	0.0135 (19)

Geometric parameters (Å, º)

Br1—C2	1.885 (4)	C5—C9	1.422 (6)
Br2—C4	1.887 (4)	C6—C7	1.360 (8)
Br3—C19	1.882 (4)	C6—H6	0.9500
Br4—C21	1.897 (4)	C7—C8	1.396 (7)
Zn1—N1	2.014 (3)	C7—H7	0.9500
Zn1—N4	2.031 (3)	C8—H8	0.9500
Zn1—N3	2.096 (3)	C10—C15	1.380 (6)
Zn1—N2	2.108 (3)	C10—C11	1.384 (6)
S1—O2	1.442 (3)	C11—C12	1.381 (6)
S1—O1	1.447 (3)	C11—H11	0.9500
S1—N1	1.600 (3)	C12—C13	1.383 (7)
S1—C10	1.777 (4)	C12—C16	1.487 (6)
S2—O4	1.435 (3)	C13—C14	1.383 (7)
S2—O3	1.462 (3)	C13—H13	0.9500
S2—N3	1.589 (3)	C14—C15	1.389 (7)
S2—C27	1.780 (4)	C14—C17	1.501 (7)
F1—C16	1.323 (6)	C15—H15	0.9500
F2—C16	1.340 (6)	C18—C19	1.386 (6)
F3—C16	1.327 (6)	C18—C26	1.431 (5)
F4—C17	1.298 (7)	C19—C20	1.408 (6)
F5—C17	1.310 (8)	C20—C21	1.357 (6)
F6—C17	1.291 (7)	C20—H20	0.9500
F7—C33	1.333 (6)	C21—C22	1.421 (6)
F8—C33	1.305 (6)	C22—C23	1.414 (6)
F9—C33	1.317 (6)	C22—C26	1.417 (5)
F10—C34	1.330 (6)	C23—C24	1.370 (6)
F11—C34	1.333 (5)	C23—H23	0.9500
F12—C34	1.330 (6)	C24—C25	1.387 (6)
N1—C1	1.404 (5)	C24—H24	0.9500
N2—C8	1.323 (6)	C25—H25	0.9500
N2—C9	1.368 (5)	C27—C32	1.382 (6)
N3—C18	1.404 (5)	C27—C28	1.390 (6)
N4—C25	1.324 (5)	C28—C29	1.382 (6)
N4—C26	1.368 (5)	C28—H28	0.9500
C1—C2	1.370 (6)	C29—C30	1.390 (6)
C1—C9	1.432 (6)	C29—C33	1.499 (6)
C2—C3	1.402 (6)	C30—C31	1.379 (6)
C3—C4	1.354 (7)	C30—H30	0.9500
C3—H3	0.9500	C31—C32	1.386 (6)
C4—C5	1.414 (7)	C31—C34	1.493 (6)
C5—C6	1.407 (7)	C32—H32	0.9500
N1—Zn1—N4	140.30 (13)	C13—C14—C17	120.2 (4)
N1—Zn1—N3	109.20 (13)	C15—C14—C17	118.7 (4)
N4—Zn1—N3	80.85 (13)	C10—C15—C14	118.4 (4)
N1—Zn1—N2	80.92 (14)	C10—C15—H15	120.8
N4—Zn1—N2	108.37 (14)	C14—C15—H15	120.8
N3—Zn1—N2	152.12 (14)	F1—C16—F3	107.9 (5)
O2—S1—O1	118.30 (19)	F1—C16—F2	105.8 (4)
O2—S1—N1	112.64 (18)	F3—C16—F2	104.5 (4)
O1—S1—N1	105.98 (18)	F1—C16—C12	113.4 (4)
O2—S1—C10	108.03 (19)	F3—C16—C12	113.1 (4)
O1—S1—C10	104.86 (19)	F2—C16—C12	111.5 (4)
N1—S1—C10	106.16 (19)	F6—C17—F4	108.2 (6)
O4—S2—O3	118.42 (19)	F6—C17—F5	102.3 (6)
O4—S2—N3	114.91 (18)	F4—C17—F5	106.6 (6)
O3—S2—N3	103.33 (18)	F6—C17—C14	112.6 (5)
O4—S2—C27	107.10 (18)	F4—C17—C14	113.9 (5)
O3—S2—C27	103.74 (18)	F5—C17—C14	112.4 (5)
N3—S2—C27	108.53 (19)	C19—C18—N3	127.4 (4)
O4—S2—Zn1	130.46 (13)	C19—C18—C26	116.5 (4)
O3—S2—Zn1	56.18 (12)	N3—C18—C26	115.9 (3)
N3—S2—Zn1	47.57 (12)	C18—C19—C20	122.5 (4)
C27—S2—Zn1	122.26 (14)	C18—C19—Br3	120.5 (3)
S2—O3—Zn1	92.49 (15)	C20—C19—Br3	117.0 (3)
C1—N1—S1	120.7 (3)	C21—C20—C19	119.6 (4)
C1—N1—Zn1	111.2 (3)	C21—C20—H20	120.2
S1—N1—Zn1	108.90 (18)	C19—C20—H20	120.2
C8—N2—C9	119.1 (4)	C20—C21—C22	122.1 (4)
C8—N2—Zn1	130.3 (3)	C20—C21—Br4	119.1 (3)
C9—N2—Zn1	109.2 (3)	C22—C21—Br4	118.7 (3)
C18—N3—S2	120.8 (3)	C23—C22—C26	118.3 (4)
C18—N3—Zn1	111.3 (2)	C23—C22—C21	124.8 (4)
S2—N3—Zn1	98.42 (17)	C26—C22—C21	116.8 (4)
C25—N4—C26	119.5 (3)	C24—C23—C22	119.3 (4)
C25—N4—Zn1	126.5 (3)	C24—C23—H23	120.3
C26—N4—Zn1	113.7 (3)	C22—C23—H23	120.3
C2—C1—N1	126.8 (4)	C23—C24—C25	119.1 (4)
C2—C1—C9	117.2 (4)	C23—C24—H24	120.5
N1—C1—C9	115.9 (3)	C25—C24—H24	120.5
C1—C2—C3	122.6 (4)	N4—C25—C24	123.2 (4)
C1—C2—Br1	121.0 (3)	N4—C25—H25	118.4
C3—C2—Br1	116.4 (3)	C24—C25—H25	118.4
C4—C3—C2	119.7 (4)	N4—C26—C22	120.3 (4)
C4—C3—H3	120.1	N4—C26—C18	117.4 (3)
C2—C3—H3	120.1	C22—C26—C18	122.3 (4)
C3—C4—C5	121.9 (4)	C32—C27—C28	121.4 (4)
C3—C4—Br2	117.1 (3)	C32—C27—S2	120.9 (3)
C5—C4—Br2	120.9 (4)	C28—C27—S2	117.6 (3)
C6—C5—C4	125.3 (4)	C29—C28—C27	118.5 (4)
C6—C5—C9	117.5 (4)	C29—C28—H28	120.8
C4—C5—C9	117.2 (4)	C27—C28—H28	120.8
C7—C6—C5	119.8 (4)	C28—C29—C30	120.8 (4)
C7—C6—H6	120.1	C28—C29—C33	119.2 (4)
C5—C6—H6	120.1	C30—C29—C33	119.9 (4)
C6—C7—C8	119.7 (5)	C31—C30—C29	119.7 (4)
C6—C7—H7	120.1	C31—C30—H30	120.2
C8—C7—H7	120.1	C29—C30—H30	120.2
N2—C8—C7	122.5 (5)	C30—C31—C32	120.5 (4)
N2—C8—H8	118.7	C30—C31—C34	120.3 (4)
C7—C8—H8	118.7	C32—C31—C34	119.3 (4)
N2—C9—C5	121.2 (4)	C27—C32—C31	119.1 (4)
N2—C9—C1	117.4 (4)	C27—C32—H32	120.4
C5—C9—C1	121.3 (4)	C31—C32—H32	120.4
C15—C10—C11	121.6 (4)	F8—C33—F9	108.9 (5)
C15—C10—S1	120.0 (3)	F8—C33—F7	105.6 (4)
C11—C10—S1	118.4 (3)	F9—C33—F7	105.5 (4)
C12—C11—C10	118.9 (4)	F8—C33—C29	113.2 (4)
C12—C11—H11	120.6	F9—C33—C29	111.3 (4)
C10—C11—H11	120.6	F7—C33—C29	111.9 (4)
C11—C12—C13	120.9 (4)	F10—C34—F12	106.1 (4)
C11—C12—C16	121.0 (4)	F10—C34—F11	106.2 (4)
C13—C12—C16	118.2 (4)	F12—C34—F11	107.4 (4)
C14—C13—C12	119.1 (4)	F10—C34—C31	112.3 (4)
C14—C13—H13	120.4	F12—C34—C31	112.1 (4)
C12—C13—H13	120.4	F11—C34—C31	112.3 (4)
C13—C14—C15	121.1 (4)
N1—Zn1—S2—O4	−176.7 (2)	C4—C5—C9—N2	−177.5 (4)
N4—Zn1—S2—O4	30.5 (2)	C6—C5—C9—C1	−177.6 (4)
N3—Zn1—S2—O4	88.3 (2)	C4—C5—C9—C1	1.0 (6)
N2—Zn1—S2—O4	−86.4 (2)	C2—C1—C9—N2	175.1 (4)
O3—Zn1—S2—O4	−100.5 (2)	N1—C1—C9—N2	−2.0 (5)
N1—Zn1—S2—O3	−76.26 (18)	C2—C1—C9—C5	−3.5 (6)
N4—Zn1—S2—O3	130.92 (18)	N1—C1—C9—C5	179.4 (3)
N3—Zn1—S2—O3	−171.2 (2)	O2—S1—C10—C15	4.0 (4)
N2—Zn1—S2—O3	14.05 (19)	O1—S1—C10—C15	−123.1 (4)
N1—Zn1—S2—N3	94.98 (19)	N1—S1—C10—C15	125.0 (4)
N4—Zn1—S2—N3	−57.84 (19)	O2—S1—C10—C11	−176.7 (3)
N2—Zn1—S2—N3	−174.7 (2)	O1—S1—C10—C11	56.3 (4)
O3—Zn1—S2—N3	171.2 (2)	N1—S1—C10—C11	−55.7 (4)
N1—Zn1—S2—C27	8.87 (19)	C15—C10—C11—C12	−1.1 (7)
N4—Zn1—S2—C27	−143.95 (19)	S1—C10—C11—C12	179.5 (3)
N3—Zn1—S2—C27	−86.1 (2)	C10—C11—C12—C13	2.0 (7)
N2—Zn1—S2—C27	99.2 (2)	C10—C11—C12—C16	−176.4 (4)
O3—Zn1—S2—C27	85.1 (2)	C11—C12—C13—C14	−1.8 (7)
O4—S2—O3—Zn1	121.71 (16)	C16—C12—C13—C14	176.6 (5)
N3—S2—O3—Zn1	−6.63 (17)	C12—C13—C14—C15	0.7 (8)
C27—S2—O3—Zn1	−119.84 (16)	C12—C13—C14—C17	−179.0 (5)
N1—Zn1—O3—S2	111.97 (16)	C11—C10—C15—C14	0.1 (7)
N4—Zn1—O3—S2	−57.91 (19)	S1—C10—C15—C14	179.4 (4)
N3—Zn1—O3—S2	5.39 (14)	C13—C14—C15—C10	0.1 (7)
N2—Zn1—O3—S2	−167.65 (16)	C17—C14—C15—C10	179.9 (5)
O2—S1—N1—C1	6.4 (4)	C11—C12—C16—F1	4.9 (7)
O1—S1—N1—C1	137.2 (3)	C13—C12—C16—F1	−173.5 (5)
C10—S1—N1—C1	−111.6 (3)	C11—C12—C16—F3	−118.4 (5)
O2—S1—N1—Zn1	−124.00 (19)	C13—C12—C16—F3	63.2 (6)
O1—S1—N1—Zn1	6.8 (2)	C11—C12—C16—F2	124.1 (5)
C10—S1—N1—Zn1	118.0 (2)	C13—C12—C16—F2	−54.3 (6)
N4—Zn1—N1—C1	−128.0 (3)	C13—C14—C17—F6	−122.5 (6)
N3—Zn1—N1—C1	133.0 (3)	C15—C14—C17—F6	57.7 (8)
N2—Zn1—N1—C1	−20.1 (3)	C13—C14—C17—F4	1.2 (9)
O3—Zn1—N1—C1	66.0 (3)	C15—C14—C17—F4	−178.5 (6)
S2—Zn1—N1—C1	96.9 (2)	C13—C14—C17—F5	122.7 (6)
N4—Zn1—N1—S1	7.3 (3)	C15—C14—C17—F5	−57.1 (7)
N3—Zn1—N1—S1	−91.60 (19)	S2—N3—C18—C19	71.6 (5)
N2—Zn1—N1—S1	115.24 (19)	Zn1—N3—C18—C19	−173.9 (3)
O3—Zn1—N1—S1	−158.64 (16)	S2—N3—C18—C26	−112.4 (4)
S2—Zn1—N1—S1	−127.77 (15)	Zn1—N3—C18—C26	2.1 (4)
N1—Zn1—N2—C8	−174.9 (4)	N3—C18—C19—C20	175.2 (4)
N4—Zn1—N2—C8	−34.8 (4)	C26—C18—C19—C20	−0.7 (6)
N3—Zn1—N2—C8	70.9 (5)	N3—C18—C19—Br3	−3.7 (6)
O3—Zn1—N2—C8	84.5 (4)	C26—C18—C19—Br3	−179.7 (3)
S2—Zn1—N2—C8	77.2 (4)	C18—C19—C20—C21	−0.2 (6)
N1—Zn1—N2—C9	18.9 (3)	Br3—C19—C20—C21	178.8 (3)
N4—Zn1—N2—C9	159.1 (3)	C19—C20—C21—C22	1.9 (6)
N3—Zn1—N2—C9	−95.3 (4)	C19—C20—C21—Br4	−177.5 (3)
O3—Zn1—N2—C9	−81.7 (3)	C20—C21—C22—C23	174.5 (4)
S2—Zn1—N2—C9	−89.0 (3)	Br4—C21—C22—C23	−6.1 (6)
O4—S2—N3—C18	−2.0 (4)	C20—C21—C22—C26	−2.6 (6)
O3—S2—N3—C18	128.5 (3)	Br4—C21—C22—C26	176.8 (3)
C27—S2—N3—C18	−121.9 (3)	C26—C22—C23—C24	0.9 (6)
Zn1—S2—N3—C18	121.0 (4)	C21—C22—C23—C24	−176.2 (4)
O4—S2—N3—Zn1	−123.02 (17)	C22—C23—C24—C25	−3.9 (6)
O3—S2—N3—Zn1	7.47 (19)	C26—N4—C25—C24	0.2 (6)
C27—S2—N3—Zn1	117.15 (17)	Zn1—N4—C25—C24	−174.1 (3)
N1—Zn1—N3—C18	134.7 (3)	C23—C24—C25—N4	3.5 (7)
N4—Zn1—N3—C18	−5.6 (3)	C25—N4—C26—C22	−3.3 (6)
N2—Zn1—N3—C18	−117.8 (3)	Zn1—N4—C26—C22	171.7 (3)
O3—Zn1—N3—C18	−132.8 (3)	C25—N4—C26—C18	175.2 (4)
S2—Zn1—N3—C18	−127.8 (3)	Zn1—N4—C26—C18	−9.8 (4)
N1—Zn1—N3—S2	−97.51 (17)	C23—C22—C26—N4	2.8 (6)
N4—Zn1—N3—S2	122.21 (18)	C21—C22—C26—N4	−180.0 (4)
N2—Zn1—N3—S2	10.0 (4)	C23—C22—C26—C18	−175.7 (4)
O3—Zn1—N3—S2	−5.01 (13)	C21—C22—C26—C18	1.6 (6)
N1—Zn1—N4—C25	73.8 (4)	C19—C18—C26—N4	−178.5 (4)
N3—Zn1—N4—C25	−177.1 (4)	N3—C18—C26—N4	5.0 (5)
N2—Zn1—N4—C25	−24.2 (4)	C19—C18—C26—C22	0.0 (6)
O3—Zn1—N4—C25	−121.9 (3)	N3—C18—C26—C22	−176.5 (4)
S2—Zn1—N4—C25	−148.4 (3)	O4—S2—C27—C32	170.4 (3)
N1—Zn1—N4—C26	−100.8 (3)	O3—S2—C27—C32	44.4 (4)
N3—Zn1—N4—C26	8.3 (3)	N3—S2—C27—C32	−65.0 (4)
N2—Zn1—N4—C26	161.2 (3)	Zn1—S2—C27—C32	−14.0 (4)
O3—Zn1—N4—C26	63.5 (3)	O4—S2—C27—C28	−7.4 (4)
S2—Zn1—N4—C26	37.0 (3)	O3—S2—C27—C28	−133.4 (3)
S1—N1—C1—C2	72.4 (5)	N3—S2—C27—C28	117.2 (3)
Zn1—N1—C1—C2	−158.3 (3)	Zn1—S2—C27—C28	168.2 (3)
S1—N1—C1—C9	−110.9 (4)	C32—C27—C28—C29	0.4 (6)
Zn1—N1—C1—C9	18.5 (4)	S2—C27—C28—C29	178.2 (3)
N1—C1—C2—C3	−179.9 (4)	C27—C28—C29—C30	−1.3 (7)
C9—C1—C2—C3	3.4 (6)	C27—C28—C29—C33	177.1 (4)
N1—C1—C2—Br1	2.0 (6)	C28—C29—C30—C31	0.9 (7)
C9—C1—C2—Br1	−174.7 (3)	C33—C29—C30—C31	−177.4 (4)
C1—C2—C3—C4	−0.7 (6)	C29—C30—C31—C32	0.4 (7)
Br1—C2—C3—C4	177.5 (3)	C29—C30—C31—C34	−179.6 (4)
C2—C3—C4—C5	−2.0 (6)	C28—C27—C32—C31	0.9 (6)
C2—C3—C4—Br2	178.3 (3)	S2—C27—C32—C31	−176.8 (3)
C3—C4—C5—C6	−179.7 (4)	C30—C31—C32—C27	−1.3 (6)
Br2—C4—C5—C6	0.1 (6)	C34—C31—C32—C27	178.7 (4)
C3—C4—C5—C9	1.8 (6)	C28—C29—C33—F8	157.7 (5)
Br2—C4—C5—C9	−178.5 (3)	C30—C29—C33—F8	−23.9 (7)
C4—C5—C6—C7	−179.4 (4)	C28—C29—C33—F9	−79.3 (6)
C9—C5—C6—C7	−0.8 (6)	C30—C29—C33—F9	99.1 (5)
C5—C6—C7—C8	−2.0 (7)	C28—C29—C33—F7	38.5 (6)
C9—N2—C8—C7	0.9 (6)	C30—C29—C33—F7	−143.1 (4)
Zn1—N2—C8—C7	−164.1 (3)	C30—C31—C34—F10	112.2 (5)
C6—C7—C8—N2	2.0 (7)	C32—C31—C34—F10	−67.9 (6)
C8—N2—C9—C5	−3.9 (6)	C30—C31—C34—F12	−128.4 (4)
Zn1—N2—C9—C5	164.1 (3)	C32—C31—C34—F12	51.6 (6)
C8—N2—C9—C1	177.5 (4)	C30—C31—C34—F11	−7.5 (7)
Zn1—N2—C9—C1	−14.5 (4)	C32—C31—C34—F11	172.5 (4)
C6—C5—C9—N2	3.8 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···O4^i	0.95	2.30	3.127 (5)	145

Symmetry code: (i) −x, −y+2, −z.