{4-Bromo-2-[(2-{(ethyl-sulfan-yl)[(2-oxido-benzyl-idene-κO)amino-κN]methyl-idene}hydrazinyl-idene-κN (1))meth-yl]phenolato-κO}(ethanol-κO)dioxido-uranium(VI).

In the title complex, [U(C17H14BrN3O2S)O2(C2H5OH)], the U(VI) cation has a distorted penta-gonal-bipyramidal environment with the penta-gonal plane defined by two N and two O atoms of the tetra-dentate Schiff base ligand and the O atom of the ethanol mol-ecule. Two oxide O atoms occupy the axial positions. The azomethine C=N group and the Br atom are disordered over two positions in a 0.8356 (18):0.1644 (18) ratio. The ethyl-thiolyl group is disordered over three conformations in a 0.8356 (18):0.085 (6):0.079 (6) ratio, and the ethanol ligand is also disordered over three orientations in a 0.470 (16):0.277 (19):0.253 (18) ratio. In the crystal, mol-ecules form centrosymmetric dimers through hydrogen bonding between ethanol O-H donors and phenolate O-atom acceptors. Weak C-H⋯O inter-actions consolidate the crystal packing.

Related literature

For semiconductor materials containing heterocycles, see: Centore, Ricciotti et al. (2012 ▶). For the structural and theoret­ical analysis of conjugation in sulfur-containing n class="Chemical">metal­organic compounds, see: Takjoo et al. (2011 ▶); Takjoo & Centore (2013 ▶). For recent examples of hydrogen bonding in crystals, see: Centore et al. (2013 ▶). For the structure of a related complex, see: Takjoo et al. (2012 ▶).

Experimental

Crystal data

[U(C17H14BrN3O2S)O2(C2H6O)]

M = 720.38

Triclinic,

a = 10.3720 (17) Å

b = 11.1380 (14) Å

c = 11.167 (1) Å

α = 69.428 (10)°

β = 86.870 (11)°

γ = 70.379 (10)°

V = 1134.7 (3) Å3

Z = 2

Mo Kα radiation

μ = 9.04 mm−1

T = 293 K

0.40 × 0.20 × 0.20 mm

Data collection

Bruker–n class="Chemical">Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.123, T max = 0.265

15923 measured reflections

5207 independent reflections

4347 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.068

S = 1.08

5207 reflections

306 parameters

53 restraints

H-atom parameters constrained

Δρmax = 1.02 e Å−3

Δρmin = −1.22 e Å−3

Data collection: COLLECT (Nonius, 1999 ▶); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000 ▶); data reduction: EVALCCD (Duisenberg et al., 2003 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molen class="Chemical">cular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813014669/cv5416sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014669/cv5416Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[U(C17H14BrN3O2S)O2(C2H6O)]	Z = 2
Mr = 720.38	F(000) = 676
Triclinic, P1	Dx = 2.109 Mg m−3
a = 10.3720 (17) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.1380 (14) Å	Cell parameters from 110 reflections
c = 11.167 (1) Å	θ = 4.6–23.6°
α = 69.428 (10)°	µ = 9.04 mm−1
β = 86.870 (11)°	T = 293 K
γ = 70.379 (10)°	Prism, red
V = 1134.7 (3) Å3	0.40 × 0.20 × 0.20 mm

Bruker–Nonius KappaCCD diffractometer	5207 independent reflections
Radiation source: normal-focus sealed tube	4347 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
Detector resolution: 9 pixels mm-1	θmax = 27.5°, θmin = 3.3°
CCD rotation images, thick slices scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −14→14
Tmin = 0.123, Tmax = 0.265	l = −14→13
15923 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.068	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0179P)2 + 1.5042P] where P = (Fo2 + 2Fc2)/3
5207 reflections	(Δ/σ)max = 0.001
306 parameters	Δρmax = 1.02 e Å−3
53 restraints	Δρmin = −1.22 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.6222 (5)	−0.4166 (5)	1.0165 (5)	0.0480 (13)
H1B	0.6535	−0.4967	1.0874	0.058*	0.1644 (18)
Br1A	0.68347 (8)	−0.57406 (7)	1.16068 (8)	0.0615 (2)	0.8356 (18)
Br1B	−0.0277 (5)	0.9058 (5)	0.2778 (5)	0.0882 (18)	0.1644 (18)
C2	0.6697 (6)	−0.4110 (6)	0.8960 (6)	0.0547 (14)
H2	0.7339	−0.4884	0.8871	0.066*
C3	0.6239 (5)	−0.2946 (6)	0.7911 (6)	0.0494 (13)
H3	0.6578	−0.2935	0.7120	0.059*
C4	0.5257 (5)	−0.1758 (5)	0.8013 (5)	0.0399 (11)
O1	0.4757 (4)	−0.0655 (3)	0.6971 (3)	0.0439 (8)
C5	0.4789 (5)	−0.1789 (5)	0.9220 (5)	0.0389 (11)
C6	0.5280 (5)	−0.3005 (5)	1.0281 (5)	0.0436 (12)
H6	0.4962	−0.3027	1.1081	0.052*
C7	0.3759 (5)	−0.0669 (5)	0.9449 (5)	0.0405 (11)
H7	0.3427	−0.0849	1.0261	0.049*
N1	0.3248 (4)	0.0560 (4)	0.8644 (4)	0.0395 (9)
N2A	0.2242 (5)	0.1373 (5)	0.9202 (4)	0.0480 (11)	0.8356 (18)
N2B	0.1747 (5)	0.2653 (5)	0.8539 (5)	0.0441 (11)	0.1644 (18)
C8A	0.1747 (5)	0.2653 (5)	0.8539 (5)	0.0441 (11)	0.8356 (18)
S1A	0.05176 (18)	0.36638 (19)	0.92399 (19)	0.0574 (5)	0.8356 (18)
C16A	0.0450 (13)	0.2473 (13)	1.0815 (13)	0.088 (4)	0.8356 (18)
H16A	0.1376	0.1892	1.1170	0.106*	0.8356 (18)
H16B	0.0039	0.2972	1.1377	0.106*	0.8356 (18)
C17A	−0.0377 (13)	0.1597 (13)	1.0763 (14)	0.128 (5)	0.8356 (18)
H17A	−0.0391	0.0973	1.1611	0.192*	0.8356 (18)
H17B	0.0034	0.1094	1.0215	0.192*	0.8356 (18)
H17C	−0.1299	0.2169	1.0431	0.192*	0.8356 (18)
C8B	0.2242 (5)	0.1373 (5)	0.9202 (4)	0.0480 (11)	0.085 (6)
S1B	0.172 (3)	0.0871 (19)	1.0706 (17)	0.062 (4)*	0.085 (6)
C16B	0.027 (5)	0.231 (5)	1.075 (5)	0.088 (4)	0.085 (6)
H16C	0.0349	0.3161	1.0164	0.106*	0.085 (6)
H16D	−0.0584	0.2236	1.0522	0.106*	0.085 (6)
C17B	0.033 (7)	0.223 (6)	1.213 (5)	0.128 (5)	0.085 (6)
H17D	−0.0425	0.2959	1.2242	0.192*	0.085 (6)
H17E	0.1179	0.2315	1.2326	0.192*	0.085 (6)
H17F	0.0279	0.1372	1.2687	0.192*	0.085 (6)
C8C	0.2242 (5)	0.1373 (5)	0.9202 (4)	0.0480 (11)	0.079 (6)
S1C	0.127 (3)	0.0792 (19)	1.043 (2)	0.062 (4)*	0.079 (6)
C16C	0.027 (5)	0.231 (5)	1.075 (5)	0.088 (4)	0.079 (6)
H16E	0.0571	0.3054	1.0221	0.106*	0.079 (6)
H16F	−0.0683	0.2541	1.0474	0.106*	0.079 (6)
C17C	0.033 (7)	0.223 (6)	1.213 (5)	0.128 (5)	0.079 (6)
H17G	−0.0321	0.3043	1.2208	0.192*	0.079 (6)
H17H	0.1237	0.2152	1.2372	0.192*	0.079 (6)
H17I	0.0116	0.1451	1.2674	0.192*	0.079 (6)
N3	0.2190 (4)	0.3221 (4)	0.7343 (4)	0.0399 (9)
C9	0.1450 (5)	0.4453 (5)	0.6638 (6)	0.0464 (12)
H9	0.0654	0.4855	0.6980	0.056*
C10	0.1708 (5)	0.5257 (5)	0.5413 (6)	0.0446 (12)
C11	0.0656 (6)	0.6486 (6)	0.4747 (6)	0.0568 (15)
H11	−0.0168	0.6753	0.5115	0.068*
C12	0.0856 (7)	0.7270 (5)	0.3570 (7)	0.0654 (17)
H12A	0.0141	0.8059	0.3125	0.079*	0.8356 (18)
C13	0.2068 (8)	0.6951 (7)	0.3002 (7)	0.0682 (18)
H13	0.2172	0.7523	0.2193	0.082*
C14	0.3117 (7)	0.5792 (7)	0.3632 (6)	0.0593 (15)
H14	0.3943	0.5580	0.3253	0.071*
C15	0.2972 (6)	0.4909 (6)	0.4848 (6)	0.0460 (12)
O2	0.3995 (4)	0.3803 (4)	0.5465 (4)	0.0528 (9)
O3	0.5501 (4)	0.1468 (4)	0.7532 (4)	0.0489 (9)
O4	0.2827 (3)	0.1828 (4)	0.5463 (4)	0.0466 (8)
U1	0.415731 (18)	0.164807 (19)	0.650973 (18)	0.03560 (6)
O5A	0.5794 (4)	0.1272 (4)	0.4954 (4)	0.0483 (9)	0.470 (16)
H5A	0.5486	0.0995	0.4528	0.058*	0.470 (16)
C18A	0.7137 (10)	0.1409 (15)	0.4828 (12)	0.042 (3)*	0.470 (16)
H18A	0.7110	0.2233	0.4958	0.051*	0.470 (16)
H18B	0.7430	0.1464	0.3976	0.051*	0.470 (16)
C19A	0.8114 (16)	0.0191 (16)	0.581 (2)	0.106 (8)	0.470 (16)
H19A	0.9024	0.0233	0.5713	0.159*	0.470 (16)
H19B	0.8096	−0.0622	0.5706	0.159*	0.470 (16)
H19C	0.7849	0.0177	0.6653	0.159*	0.470 (16)
O5B	0.5794 (4)	0.1272 (4)	0.4954 (4)	0.0483 (9)	0.277 (19)
H5B	0.5487	0.0992	0.4535	0.058*	0.277 (19)
C18B	0.683 (2)	0.192 (3)	0.462 (3)	0.072 (9)*	0.277 (19)
H18C	0.7096	0.2071	0.5353	0.086*	0.277 (19)
H18D	0.6448	0.2796	0.3935	0.086*	0.277 (19)
C19B	0.8029 (17)	0.1076 (18)	0.4192 (18)	0.104 (6)*	0.277 (19)
H19D	0.8752	0.1452	0.4103	0.156*	0.277 (19)
H19E	0.7799	0.1053	0.3382	0.156*	0.277 (19)
H19F	0.8329	0.0167	0.4814	0.156*	0.277 (19)
O5C	0.5794 (4)	0.1272 (4)	0.4954 (4)	0.0483 (9)	0.253 (18)
H5C	0.5476	0.1003	0.4533	0.058*	0.253 (18)
C18C	0.7286 (16)	0.073 (3)	0.531 (2)	0.055 (8)*	0.253 (18)
H18E	0.7482	0.1098	0.5917	0.067*	0.253 (18)
H18F	0.7579	−0.0258	0.5721	0.067*	0.253 (18)
C19C	0.8029 (17)	0.1076 (18)	0.4192 (18)	0.104 (6)*	0.253 (18)
H19G	0.8995	0.0713	0.4436	0.156*	0.253 (18)
H19H	0.7750	0.2050	0.3796	0.156*	0.253 (18)
H19I	0.7840	0.0700	0.3597	0.156*	0.253 (18)

	U11	U22	U33	U12	U13	U23
C1	0.047 (3)	0.045 (3)	0.043 (3)	−0.007 (2)	−0.012 (2)	−0.011 (2)
Br1A	0.0653 (5)	0.0427 (4)	0.0608 (5)	−0.0068 (3)	−0.0091 (4)	−0.0090 (3)
Br1B	0.083 (3)	0.083 (3)	0.087 (4)	−0.036 (3)	−0.015 (3)	−0.005 (3)
C2	0.046 (3)	0.053 (3)	0.060 (4)	0.000 (3)	−0.001 (3)	−0.029 (3)
C3	0.047 (3)	0.050 (3)	0.047 (3)	−0.001 (2)	0.005 (2)	−0.027 (3)
C4	0.041 (3)	0.043 (3)	0.038 (3)	−0.011 (2)	0.001 (2)	−0.019 (2)
O1	0.056 (2)	0.0418 (19)	0.0314 (18)	−0.0056 (16)	0.0018 (16)	−0.0199 (15)
C5	0.038 (2)	0.044 (3)	0.038 (3)	−0.010 (2)	0.000 (2)	−0.021 (2)
C6	0.048 (3)	0.045 (3)	0.037 (3)	−0.011 (2)	−0.001 (2)	−0.017 (2)
C7	0.044 (3)	0.045 (3)	0.031 (3)	−0.011 (2)	0.005 (2)	−0.016 (2)
N1	0.040 (2)	0.042 (2)	0.035 (2)	−0.0048 (18)	0.0051 (17)	−0.0205 (18)
N2A	0.046 (2)	0.054 (3)	0.044 (3)	−0.008 (2)	0.014 (2)	−0.027 (2)
N2B	0.041 (3)	0.049 (3)	0.046 (3)	−0.010 (2)	0.009 (2)	−0.027 (2)
C8A	0.041 (3)	0.049 (3)	0.046 (3)	−0.010 (2)	0.009 (2)	−0.027 (2)
S1A	0.0515 (10)	0.0548 (10)	0.0647 (12)	−0.0065 (8)	0.0199 (8)	−0.0330 (9)
C16A	0.098 (7)	0.074 (6)	0.097 (7)	−0.026 (5)	0.059 (5)	−0.046 (5)
C17A	0.147 (11)	0.111 (9)	0.149 (13)	−0.061 (9)	0.077 (10)	−0.066 (9)
C8B	0.046 (2)	0.054 (3)	0.044 (3)	−0.008 (2)	0.014 (2)	−0.027 (2)
C16B	0.098 (7)	0.074 (6)	0.097 (7)	−0.026 (5)	0.059 (5)	−0.046 (5)
C17B	0.147 (11)	0.111 (9)	0.149 (13)	−0.061 (9)	0.077 (10)	−0.066 (9)
C8C	0.046 (2)	0.054 (3)	0.044 (3)	−0.008 (2)	0.014 (2)	−0.027 (2)
C16C	0.098 (7)	0.074 (6)	0.097 (7)	−0.026 (5)	0.059 (5)	−0.046 (5)
C17C	0.147 (11)	0.111 (9)	0.149 (13)	−0.061 (9)	0.077 (10)	−0.066 (9)
N3	0.039 (2)	0.042 (2)	0.043 (2)	−0.0112 (18)	0.0030 (18)	−0.0221 (19)
C9	0.037 (3)	0.044 (3)	0.061 (4)	−0.007 (2)	0.002 (2)	−0.028 (3)
C10	0.045 (3)	0.039 (3)	0.054 (3)	−0.014 (2)	−0.001 (2)	−0.019 (2)
C11	0.050 (3)	0.048 (3)	0.069 (4)	−0.012 (3)	−0.009 (3)	−0.020 (3)
C12	0.073 (4)	0.052 (4)	0.064 (4)	−0.023 (3)	−0.015 (3)	−0.006 (3)
C13	0.083 (5)	0.067 (4)	0.054 (4)	−0.036 (4)	−0.005 (3)	−0.008 (3)
C14	0.067 (4)	0.064 (4)	0.055 (4)	−0.034 (3)	0.010 (3)	−0.021 (3)
C15	0.048 (3)	0.045 (3)	0.052 (3)	−0.020 (2)	0.000 (2)	−0.021 (3)
O2	0.046 (2)	0.047 (2)	0.067 (3)	−0.0162 (17)	0.0111 (19)	−0.0222 (19)
O3	0.0410 (19)	0.068 (2)	0.045 (2)	−0.0157 (18)	0.0043 (16)	−0.0310 (19)
O4	0.0400 (18)	0.054 (2)	0.049 (2)	−0.0104 (16)	−0.0014 (16)	−0.0258 (18)
U1	0.03288 (9)	0.04260 (11)	0.03333 (10)	−0.00789 (7)	0.00249 (6)	−0.02045 (7)
O5A	0.0432 (19)	0.071 (3)	0.044 (2)	−0.0205 (18)	0.0099 (16)	−0.0346 (19)
C19A	0.057 (9)	0.090 (13)	0.17 (2)	−0.011 (9)	−0.029 (12)	−0.051 (14)
O5B	0.0432 (19)	0.071 (3)	0.044 (2)	−0.0205 (18)	0.0099 (16)	−0.0346 (19)
O5C	0.0432 (19)	0.071 (3)	0.044 (2)	−0.0205 (18)	0.0099 (16)	−0.0346 (19)

C1—C6	1.378 (7)	C9—H9	0.9300
C1—C2	1.395 (8)	C10—C11	1.410 (7)
C1—Br1A	1.858 (5)	C10—C15	1.417 (8)
C1—H1B	0.9300	C11—C12	1.348 (9)
C2—C3	1.364 (8)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.372 (10)
C3—C4	1.410 (7)	C12—H12A	0.9300
C3—H3	0.9300	C13—C14	1.360 (9)
C4—O1	1.328 (6)	C13—H13	0.9300
C4—C5	1.400 (7)	C14—C15	1.404 (8)
O1—U1	2.295 (3)	C14—H14	0.9300
C5—C6	1.405 (7)	C15—O2	1.312 (7)
C5—C7	1.436 (7)	O2—U1	2.221 (4)
C6—H6	0.9300	O3—U1	1.764 (4)
C7—N1	1.290 (6)	O4—U1	1.771 (3)
C7—H7	0.9300	U1—O5A	2.406 (3)
N1—N2A	1.410 (5)	O5A—C18A	1.445 (10)
N1—U1	2.556 (4)	O5A—H5A	0.7809
S1A—C16A	1.808 (13)	O5A—H5B	0.7768
C16A—C17A	1.517 (9)	O5A—H5C	0.7761
C16A—H16A	0.9700	C18A—C19A	1.492 (9)
C16A—H16B	0.9700	C18A—H18A	0.9700
C17A—H17A	0.9600	C18A—H18B	0.9700
C17A—H17B	0.9600	C19A—H19A	0.9600
C17A—H17C	0.9600	C19A—H19B	0.9600
S1B—C16B	1.81 (3)	C19A—H19C	0.9600
C16B—C17B	1.52 (2)	C18B—C19B	1.455 (18)
C16B—H16C	0.9700	C18B—H18C	0.9700
C16B—H16D	0.9700	C18B—H18D	0.9700
C17B—H17D	0.9600	C19B—H19D	0.9600
C17B—H17E	0.9600	C19B—H19E	0.9600
C17B—H17F	0.9600	C19B—H19F	0.9600
N3—C9	1.301 (7)	C18C—H18E	0.9700
N3—U1	2.576 (4)	C18C—H18F	0.9700
C9—C10	1.416 (8)
C6—C1—C2	118.4 (5)	C13—C12—H12A	118.6
C6—C1—Br1A	119.5 (4)	C14—C13—C12	119.4 (6)
C2—C1—Br1A	122.1 (4)	C14—C13—H13	120.3
C6—C1—H1B	120.8	C12—C13—H13	120.3
C2—C1—H1B	120.8	C13—C14—C15	121.0 (6)
Br1A—C1—H1B	1.4	C13—C14—H14	119.5
C3—C2—C1	121.4 (5)	C15—C14—H14	119.5
C3—C2—H2	119.3	O2—C15—C14	120.9 (5)
C1—C2—H2	119.3	O2—C15—C10	120.6 (5)
C2—C3—C4	120.7 (5)	C14—C15—C10	118.5 (5)
C2—C3—H3	119.7	C15—O2—U1	133.4 (3)
C4—C3—H3	119.7	O3—U1—O4	179.05 (17)
O1—C4—C5	121.2 (4)	O3—U1—O2	89.52 (17)
O1—C4—C3	120.1 (5)	O4—U1—O2	90.23 (16)
C5—C4—C3	118.6 (5)	O3—U1—O1	93.70 (16)
C4—O1—U1	134.9 (3)	O4—U1—O1	86.22 (15)
C4—C5—C6	119.3 (4)	O2—U1—O1	159.51 (13)
C4—C5—C7	124.2 (5)	O3—U1—O5A	88.85 (14)
C6—C5—C7	116.3 (5)	O4—U1—O5A	90.21 (14)
C1—C6—C5	121.5 (5)	O2—U1—O5A	82.02 (14)
C1—C6—H6	119.2	O1—U1—O5A	77.82 (13)
C5—C6—H6	119.2	O3—U1—N1	82.19 (16)
N1—C7—C5	126.6 (5)	O4—U1—N1	98.66 (16)
N1—C7—H7	116.7	O2—U1—N1	130.39 (14)
C5—C7—H7	116.7	O1—U1—N1	70.10 (12)
C7—N1—N2A	110.6 (4)	O5A—U1—N1	145.93 (13)
C7—N1—U1	127.6 (3)	O3—U1—N3	97.53 (15)
N2A—N1—U1	120.6 (3)	O4—U1—N3	83.25 (14)
C17A—C16A—S1A	111.4 (10)	O2—U1—N3	70.53 (14)
C17A—C16A—H16A	109.4	O1—U1—N3	128.83 (13)
S1A—C16A—H16A	109.4	O5A—U1—N3	151.69 (14)
C17A—C16A—H16B	109.4	N1—U1—N3	62.37 (13)
S1A—C16A—H16B	109.4	C18A—O5A—U1	129.7 (6)
H16A—C16A—H16B	108.0	C18A—O5A—H5A	123.9
C16A—C17A—H17A	109.5	U1—O5A—H5A	106.3
C16A—C17A—H17B	109.5	C18A—O5A—H5B	124.2
H17A—C17A—H17B	109.5	U1—O5A—H5B	106.0
C16A—C17A—H17C	109.5	H5A—O5A—H5B	0.4
H17A—C17A—H17C	109.5	C18A—O5A—H5C	124.8
H17B—C17A—H17C	109.5	U1—O5A—H5C	105.4
C17B—C16B—S1B	104 (2)	H5A—O5A—H5C	0.9
C17B—C16B—H16C	111.0	H5B—O5A—H5C	1.0
S1B—C16B—H16C	111.0	O5A—C18A—C19A	108.0 (10)
C17B—C16B—H16D	111.0	O5A—C18A—H18A	110.1
S1B—C16B—H16D	111.0	C19A—C18A—H18A	110.1
H16C—C16B—H16D	109.0	O5A—C18A—H18B	110.1
C16B—C17B—H17D	109.5	C19A—C18A—H18B	110.1
C16B—C17B—H17E	109.5	H18A—C18A—H18B	108.4
H17D—C17B—H17E	109.5	C18A—C19A—H19A	109.5
C16B—C17B—H17F	109.5	C18A—C19A—H19B	109.5
H17D—C17B—H17F	109.5	H19A—C19A—H19B	109.5
H17E—C17B—H17F	109.5	C18A—C19A—H19C	109.5
C9—N3—U1	123.7 (4)	H19A—C19A—H19C	109.5
N3—C9—C10	127.9 (5)	H19B—C19A—H19C	109.5
N3—C9—H9	116.0	C19B—C18B—H18C	109.4
C10—C9—H9	116.0	C19B—C18B—H18D	109.4
C11—C10—C9	117.6 (5)	H18C—C18B—H18D	108.0
C11—C10—C15	118.9 (6)	C18B—C19B—H19D	109.5
C9—C10—C15	123.5 (5)	C18B—C19B—H19E	109.5
C12—C11—C10	119.3 (6)	H19D—C19B—H19E	109.5
C12—C11—H11	120.3	C18B—C19B—H19F	109.5
C10—C11—H11	120.3	H19D—C19B—H19F	109.5
C11—C12—C13	122.8 (6)	H19E—C19B—H19F	109.5
C11—C12—H12A	118.6	H18E—C18C—H18F	108.1
C6—C1—C2—C3	−0.6 (9)	C15—O2—U1—O4	31.2 (5)
Br1A—C1—C2—C3	−179.9 (5)	C15—O2—U1—O1	111.0 (5)
C1—C2—C3—C4	−0.5 (9)	C15—O2—U1—O5A	121.4 (5)
C2—C3—C4—O1	−175.9 (5)	C15—O2—U1—N1	−70.4 (5)
C2—C3—C4—C5	1.7 (8)	C15—O2—U1—N3	−51.5 (5)
C5—C4—O1—U1	40.8 (7)	C4—O1—U1—O3	36.0 (5)
C3—C4—O1—U1	−141.7 (4)	C4—O1—U1—O4	−144.9 (5)
O1—C4—C5—C6	175.9 (5)	C4—O1—U1—O2	134.6 (5)
C3—C4—C5—C6	−1.7 (8)	C4—O1—U1—O5A	124.0 (5)
O1—C4—C5—C7	−0.2 (8)	C4—O1—U1—N1	−44.3 (4)
C3—C4—C5—C7	−177.8 (5)	C4—O1—U1—N3	−66.7 (5)
C2—C1—C6—C5	0.5 (8)	C7—N1—U1—O3	−68.2 (4)
Br1A—C1—C6—C5	179.9 (4)	N2A—N1—U1—O3	98.1 (4)
C4—C5—C6—C1	0.6 (8)	C7—N1—U1—O4	111.4 (4)
C7—C5—C6—C1	177.0 (5)	N2A—N1—U1—O4	−82.3 (4)
C4—C5—C7—N1	−9.6 (9)	C7—N1—U1—O2	−150.8 (4)
C6—C5—C7—N1	174.2 (5)	N2A—N1—U1—O2	15.5 (4)
C5—C7—N1—N2A	178.9 (5)	C7—N1—U1—O1	28.7 (4)
C5—C7—N1—U1	−13.7 (8)	N2A—N1—U1—O1	−165.0 (4)
U1—N3—C9—C10	−13.0 (8)	C7—N1—U1—O5A	8.0 (6)
N3—C9—C10—C11	170.5 (5)	N2A—N1—U1—O5A	174.3 (3)
N3—C9—C10—C15	−11.3 (9)	C7—N1—U1—N3	−170.9 (5)
C9—C10—C11—C12	−179.0 (6)	N2A—N1—U1—N3	−4.6 (3)
C15—C10—C11—C12	2.7 (8)	C9—N3—U1—O3	117.9 (4)
C10—C11—C12—C13	−2.6 (10)	C9—N3—U1—O4	−61.6 (4)
C11—C12—C13—C14	0.8 (11)	C9—N3—U1—O2	31.0 (4)
C12—C13—C14—C15	0.7 (10)	C9—N3—U1—O1	−141.2 (4)
C13—C14—C15—O2	−178.7 (6)	C9—N3—U1—O5A	16.2 (6)
C13—C14—C15—C10	−0.5 (9)	C9—N3—U1—N1	−165.1 (4)
C11—C10—C15—O2	177.0 (5)	O3—U1—O5A—C18A	−20.1 (8)
C9—C10—C15—O2	−1.1 (8)	O4—U1—O5A—C18A	159.7 (8)
C11—C10—C15—C14	−1.2 (8)	O2—U1—O5A—C18A	69.5 (8)
C9—C10—C15—C14	−179.4 (5)	O1—U1—O5A—C18A	−114.2 (8)
C14—C15—O2—U1	−133.5 (5)	N1—U1—O5A—C18A	−94.4 (8)
C10—C15—O2—U1	48.3 (7)	N3—U1—O5A—C18A	83.7 (8)
C15—O2—U1—O3	−149.7 (5)	U1—O5A—C18A—C19A	77.3 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O5A—H5A···O1i	0.78	1.89	2.618 (5)	155
C7—H7···O3ii	0.93	2.53	3.235 (6)	133
C6—H6···O3ii	0.93	2.63	3.368 (6)	137
C11—H11···O4iii	0.93	2.66	3.443 (7)	143
C19A—H19B···O4i	0.96	2.58	3.451 (19)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5A—H5A⋯O1i	0.78	1.89	2.618 (5)	155
C7—H7⋯O3ii	0.93	2.53	3.235 (6)	133
C6—H6⋯O3ii	0.93	2.63	3.368 (6)	137
C11—H11⋯O4iii	0.93	2.66	3.443 (7)	143
C19A—H19B⋯O4i	0.96	2.58	3.451 (19)	151

Symmetry codes: (i) ; (ii) ; (iii) .