(E)-2-[4-(Di-ethyl-amino)-styr-yl]-1-methyl-quinolin-1-ium 4-chloro-benzene-sulfonate monohydrate.

The asymmetric unit of the title hydrated salt, C22H25N2 (+)·C6H4ClO3S(-)·H2O, comprises two 2-[4-(di-ethyl-amino)-styr-yl]-1-methyl-quinolin-1-ium cations, two 4-chloro-benzene-sul-fon-ate anions and two solvent water mol-ecules. One ethyl group of both cations displays disorder over two positions in a 0.659 (2):0.341 (2) ratio in one mol-ecule and in a 0.501 (2):0.499 (2) ratio in the other. The sulfonate group of one anion is also disordered over two positions in a 0.893 (7):0.107 (7) ratio. The dihedral angle between the mean plane of the quinolinium ring system and that of benzene ring is 10.57 (18)° in one cation and 14.4 (2)° in the other. In the crystal, cations, anions and water mol-ecules are linked into chains along the [010] direction by O-H⋯Osulfonate hydrogen bonds, together with weak C-H⋯Osulfonate and C-H⋯Cl inter-actions. The cations are stacked by π-π inter-actions, with centroid-centroid distances in the range 3.675 (2)-4.162 (3) Å.

Related literature

For standard bond lengths, see: Allen et al. (1987 ▶). For background to and applications of quarternary ammonium compounds, see: Barchéchath et al. (2005 ▶); Chanawanno et al. (2010a ▶,b ▶); Bolden et al. (2013 ▶). For related structures, see: Chantrapromma et al. (2012 ▶); Fun, Kaewmanee et al. (2011 ▶, 2013 ▶); Kaewmanee et al. (2010 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C22H25N2 +·C6H4ClO3S−·H2O

M = 527.07

Monoclinic,

a = 25.814 (4) Å

b = 10.5563 (16) Å

c = 20.333 (3) Å

β = 110.883 (2)°

V = 5176.8 (14) Å3

Z = 8

Mo Kα radiation

μ = 0.27 mm−1

T = 100 K

0.31 × 0.19 × 0.15 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.923, T max = 0.961

28821 measured reflections

10657 independent reflections

6269 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.076

wR(F 2) = 0.201

S = 1.04

10657 reflections

708 parameters

H-atom parameters constrained

Δρmax = 0.61 e Å−3

Δρmin = −0.43 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2009 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009 ▶), Mercury (Macrae et al., 2008 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814004577/sj5390sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814004577/sj5390Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814004577/sj5390Isup3.cml

CCDC reference: 988937

Additional supporting information: crystallographic information; 3D view; checkCIF report

C22H25N2+·C6H4ClO3S−·H2O	F(000) = 2224
Mr = 527.07	Dx = 1.352 Mg m−3
Monoclinic, P21/c	Melting point = 471–473 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 25.814 (4) Å	Cell parameters from 10657 reflections
b = 10.5563 (16) Å	θ = 2–26.5°
c = 20.333 (3) Å	µ = 0.27 mm−1
β = 110.883 (2)°	T = 100 K
V = 5176.8 (14) Å3	Block, brown
Z = 8	0.31 × 0.19 × 0.15 mm

Bruker SMART APEXII DUO CCD area-detector diffractometer	10657 independent reflections
Radiation source: fine-focus sealed tube	6269 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.064
φ and ω scans	θmax = 26.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −30→32
Tmin = 0.923, Tmax = 0.961	k = −13→13
28821 measured reflections	l = −25→25

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)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.201	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0652P)2 + 7.6849P] where P = (Fo2 + 2Fc2)/3
10657 reflections	(Δ/σ)max = 0.001
708 parameters	Δρmax = 0.61 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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)
Cl1A	0.27801 (5)	0.17454 (13)	0.13432 (7)	0.0684 (4)
S1A	0.46207 (4)	0.58226 (11)	0.26409 (5)	0.0415 (3)
O1A	0.43655 (13)	0.6836 (3)	0.29041 (14)	0.0512 (8)
O2A	0.50670 (12)	0.5209 (3)	0.31975 (14)	0.0578 (9)
O3A	0.47678 (12)	0.6192 (3)	0.20454 (14)	0.0538 (8)
C23A	0.32927 (17)	0.2876 (4)	0.17242 (19)	0.0404 (10)
C24A	0.38262 (17)	0.2482 (4)	0.2059 (2)	0.0411 (10)
H24A	0.3915	0.1625	0.2090	0.049*
C25A	0.42288 (17)	0.3380 (4)	0.23497 (18)	0.0388 (9)
H25A	0.4594	0.3127	0.2578	0.047*
C26A	0.40971 (14)	0.4651 (4)	0.23066 (16)	0.0311 (8)
C27A	0.35560 (17)	0.5029 (4)	0.1966 (2)	0.0415 (10)
H27A	0.3467	0.5886	0.1933	0.050*
C28A	0.31469 (17)	0.4142 (5)	0.1674 (2)	0.0483 (11)
H28A	0.2780	0.4389	0.1447	0.058*
N1A	0.45312 (13)	0.3584 (3)	0.01622 (15)	0.0406 (8)
N2A	0.7161 (2)	−0.2368 (5)	0.1056 (2)	0.0799 (15)
C1A	0.41975 (15)	0.4623 (4)	−0.01354 (19)	0.0402 (10)
C2A	0.39663 (18)	0.5404 (5)	0.0243 (2)	0.0529 (12)
H2AA	0.4035	0.5240	0.0716	0.064*
C3A	0.3643 (2)	0.6400 (5)	−0.0077 (3)	0.0632 (13)
H3AA	0.3492	0.6909	0.0183	0.076*
C4A	0.35306 (19)	0.6681 (5)	−0.0783 (3)	0.0570 (12)
H4AA	0.3298	0.7354	−0.0995	0.068*
C5A	0.37609 (17)	0.5973 (5)	−0.1160 (2)	0.0520 (12)
H5AA	0.3695	0.6179	−0.1627	0.062*
C6A	0.41001 (16)	0.4924 (4)	−0.0853 (2)	0.0443 (10)
C7A	0.43683 (17)	0.4199 (5)	−0.12117 (19)	0.0489 (11)
H7AA	0.4310	0.4386	−0.1680	0.059*
C8A	0.47081 (18)	0.3236 (5)	−0.0897 (2)	0.0489 (11)
H8AA	0.4885	0.2782	−0.1148	0.059*
C9A	0.48013 (15)	0.2900 (4)	−0.01798 (18)	0.0388 (9)
C10A	0.51864 (16)	0.1924 (4)	0.01698 (19)	0.0412 (10)
H10A	0.5250	0.1775	0.0643	0.049*
C11A	0.54617 (16)	0.1210 (4)	−0.01445 (19)	0.0435 (10)
H11A	0.5367	0.1329	−0.0626	0.052*
C12A	0.58865 (16)	0.0282 (4)	0.01772 (18)	0.0403 (10)
C13A	0.61718 (17)	−0.0274 (4)	−0.02134 (19)	0.0460 (11)
H13A	0.6074	−0.0054	−0.0685	0.055*
C14A	0.65862 (19)	−0.1123 (5)	0.0065 (2)	0.0515 (12)
H14A	0.6770	−0.1450	−0.0217	0.062*
C15A	0.67463 (19)	−0.1524 (5)	0.0774 (2)	0.0515 (11)
C16A	0.64536 (18)	−0.0960 (4)	0.1171 (2)	0.0488 (11)
H16A	0.6543	−0.1190	0.1640	0.059*
C17A	0.60460 (16)	−0.0093 (4)	0.08862 (19)	0.0443 (10)
H17A	0.5868	0.0261	0.1167	0.053*
C18A	0.7320 (2)	−0.2810 (5)	0.1780 (2)	0.0714 (15)
H18A	0.7491	−0.3639	0.1819	0.086*
H18B	0.6990	−0.2901	0.1899	0.086*
C19A	0.7719 (2)	−0.1921 (6)	0.2300 (2)	0.0733 (16)
H19A	0.7793	−0.2224	0.2770	0.110*
H19B	0.7558	−0.1091	0.2251	0.110*
H19C	0.8059	−0.1882	0.2209	0.110*
C20A	0.7593 (5)	−0.2587 (10)	0.0703 (5)	0.056 (3)	0.66 (2)
H20A	0.7613	−0.1855	0.0424	0.067*	0.66 (2)
H20B	0.7957	−0.2733	0.1055	0.067*	0.66 (2)
C21A	0.7402 (4)	−0.3732 (10)	0.0241 (7)	0.075 (4)	0.66 (2)
H21A	0.7679	−0.3966	0.0050	0.113*	0.66 (2)
H21B	0.7061	−0.3541	−0.0137	0.113*	0.66 (2)
H21C	0.7343	−0.4422	0.0514	0.113*	0.66 (2)
C20X	0.7305 (7)	−0.3315 (18)	0.0610 (10)	0.049 (6)	0.34 (2)
H20C	0.7008	−0.3424	0.0159	0.059*	0.34 (2)
H20D	0.7401	−0.4128	0.0844	0.059*	0.34 (2)
C21X	0.7817 (9)	−0.265 (2)	0.0534 (10)	0.057 (5)	0.34 (2)
H21D	0.7937	−0.3111	0.0209	0.086*	0.34 (2)
H21E	0.8111	−0.2615	0.0984	0.086*	0.34 (2)
H21F	0.7718	−0.1801	0.0361	0.086*	0.34 (2)
C22A	0.45767 (19)	0.3216 (5)	0.0879 (2)	0.0559 (13)
H22A	0.4675	0.2336	0.0953	0.084*
H22B	0.4227	0.3352	0.0936	0.084*
H22C	0.4857	0.3719	0.1216	0.084*
Cl1B	0.22680 (5)	0.59222 (12)	0.37098 (6)	0.0612 (3)
S1B	0.04143 (5)	1.00755 (13)	0.30263 (6)	0.0579 (3)
O1B	−0.00922 (17)	0.9418 (5)	0.3027 (2)	0.0866 (18)	0.893 (7)
O2B	0.0603 (2)	1.0986 (4)	0.35813 (19)	0.0867 (19)	0.893 (7)
O3B	0.03461 (16)	1.0545 (4)	0.23477 (17)	0.0595 (13)	0.893 (7)
O1Y	0.0265 (16)	1.006 (4)	0.359 (2)	0.075 (11)*	0.107 (7)
O2Y	0.075 (2)	1.122 (5)	0.278 (3)	0.113 (17)*	0.107 (7)
O3Y	0.0062 (12)	0.977 (3)	0.2366 (14)	0.048 (9)*	0.107 (7)
C23B	0.17478 (17)	0.7065 (4)	0.35240 (19)	0.0402 (10)
C24B	0.18873 (19)	0.8286 (5)	0.3746 (2)	0.0515 (11)
H24B	0.2254	0.8500	0.3997	0.062*
C25B	0.14773 (19)	0.9191 (4)	0.3592 (2)	0.0501 (11)
H25B	0.1570	1.0021	0.3741	0.060*
C26B	0.09301 (17)	0.8887 (4)	0.32205 (19)	0.0409 (10)
C27B	0.08004 (18)	0.7646 (4)	0.3010 (2)	0.0474 (11)
H27B	0.0433	0.7425	0.2763	0.057*
C28B	0.12075 (18)	0.6726 (4)	0.3161 (2)	0.0449 (10)
H28B	0.1117	0.5892	0.3018	0.054*
N1B	1.03757 (14)	0.8261 (4)	1.05282 (18)	0.0477 (9)
N2B	0.7638 (2)	0.2637 (6)	0.8629 (2)	0.100 (2)
C1B	1.07121 (16)	0.9334 (4)	1.0564 (2)	0.0478 (11)
C2B	1.0951 (2)	1.0019 (5)	1.1184 (3)	0.0644 (14)
H2BA	1.0896	0.9767	1.1592	0.077*
C3B	1.1261 (2)	1.1042 (6)	1.1192 (3)	0.0761 (16)
H3BA	1.1421	1.1485	1.1611	0.091*
C4B	1.1352 (2)	1.1459 (5)	1.0598 (4)	0.0747 (16)
H4BA	1.1571	1.2170	1.0623	0.090*
C5B	1.1124 (2)	1.0837 (5)	0.9981 (3)	0.0654 (14)
H5BA	1.1185	1.1117	0.9581	0.079*
C6B	1.07887 (18)	0.9748 (5)	0.9949 (3)	0.0537 (12)
C7B	1.0522 (2)	0.9091 (5)	0.9319 (3)	0.0593 (13)
H7BA	1.0571	0.9355	0.8909	0.071*
C8B	1.01959 (19)	0.8085 (4)	0.9299 (2)	0.0533 (12)
H8BA	1.0021	0.7671	0.8873	0.064*
C9B	1.01126 (17)	0.7638 (4)	0.9921 (2)	0.0426 (10)
C10B	0.97260 (17)	0.6636 (4)	0.9875 (2)	0.0447 (10)
H10B	0.9677	0.6381	1.0287	0.054*
C11B	0.94348 (18)	0.6051 (4)	0.9283 (2)	0.0486 (11)
H11B	0.9526	0.6256	0.8893	0.058*
C12B	0.89936 (17)	0.5137 (4)	0.9161 (2)	0.0441 (10)
C13B	0.8711 (2)	0.4738 (5)	0.8474 (2)	0.0578 (13)
H13B	0.8823	0.5046	0.8118	0.069*
C14B	0.82772 (19)	0.3919 (5)	0.8300 (2)	0.0562 (13)
H14B	0.8104	0.3683	0.7832	0.067*
C15B	0.8085 (2)	0.3420 (5)	0.8811 (2)	0.0624 (14)
C16B	0.8378 (2)	0.3800 (6)	0.9517 (2)	0.0713 (16)
H16B	0.8274	0.3478	0.9878	0.086*
C17B	0.88144 (19)	0.4641 (5)	0.9675 (2)	0.0527 (12)
H17B	0.8994	0.4884	1.0141	0.063*
C18B	0.7377 (4)	0.2303 (11)	0.9135 (6)	0.039 (4)	0.50 (2)
H18C	0.6995	0.2045	0.8896	0.047*	0.50 (2)
H18D	0.7385	0.3013	0.9441	0.047*	0.50 (2)
C19B	0.7729 (7)	0.1191 (16)	0.9558 (7)	0.059 (4)	0.50 (2)
H19D	0.7571	0.0886	0.9890	0.089*	0.50 (2)
H19E	0.8101	0.1476	0.9806	0.089*	0.50 (2)
H19F	0.7734	0.0519	0.9242	0.089*	0.50 (2)
C18Y	0.7654 (8)	0.1500 (17)	0.9252 (11)	0.073 (5)	0.50 (2)
H18E	0.7575	0.0654	0.9055	0.087*	0.50 (2)
H18F	0.7998	0.1505	0.9655	0.087*	0.50 (2)
C19Y	0.7197 (6)	0.2047 (14)	0.9404 (7)	0.081 (5)	0.50 (2)
H19G	0.7132	0.1565	0.9768	0.122*	0.50 (2)
H19H	0.6870	0.2033	0.8987	0.122*	0.50 (2)
H19I	0.7284	0.2906	0.9558	0.122*	0.50 (2)
C20B	0.7343 (2)	0.2220 (6)	0.7893 (2)	0.0650 (14)
H20E	0.7304	0.2936	0.7580	0.078*
H20F	0.6974	0.1936	0.7845	0.078*
C21B	0.7635 (2)	0.1176 (6)	0.7675 (3)	0.0732 (15)
H21G	0.7438	0.0970	0.7190	0.110*
H21H	0.7652	0.0443	0.7961	0.110*
H21I	0.8005	0.1442	0.7733	0.110*
C22B	1.0325 (2)	0.7835 (5)	1.1179 (2)	0.0666 (14)
H22D	1.0187	0.6982	1.1123	0.100*
H22E	1.0071	0.8377	1.1296	0.100*
H22F	1.0681	0.7865	1.1550	0.100*
O1WA	0.40302 (13)	0.9141 (3)	0.21471 (18)	0.0667 (9)
H1WB	0.9111	0.8460	0.2208	0.100*
H2WB	0.9173	0.7813	0.1665	0.100*
O1WB	0.9093 (2)	0.8517 (5)	0.1784 (3)	0.1310 (19)
H1WA	0.4309	0.9315	0.2043	0.197*
H2WA	0.4077	0.8524	0.2351	0.197*

	U11	U22	U33	U12	U13	U23
Cl1A	0.0795 (8)	0.0702 (9)	0.0648 (7)	−0.0410 (7)	0.0372 (6)	−0.0300 (7)
S1A	0.0496 (6)	0.0487 (7)	0.0280 (4)	−0.0144 (5)	0.0162 (4)	−0.0073 (4)
O1A	0.071 (2)	0.0453 (18)	0.0434 (15)	−0.0149 (16)	0.0283 (15)	−0.0155 (14)
O2A	0.0490 (17)	0.079 (2)	0.0356 (14)	−0.0096 (17)	0.0026 (13)	−0.0031 (15)
O3A	0.0645 (19)	0.065 (2)	0.0391 (15)	−0.0277 (17)	0.0270 (14)	−0.0083 (14)
C23A	0.053 (2)	0.038 (2)	0.0353 (19)	−0.017 (2)	0.0216 (18)	−0.0094 (18)
C24A	0.060 (3)	0.030 (2)	0.044 (2)	0.000 (2)	0.032 (2)	0.0002 (19)
C25A	0.047 (2)	0.043 (3)	0.0308 (18)	0.004 (2)	0.0203 (17)	0.0016 (18)
C26A	0.038 (2)	0.036 (2)	0.0213 (15)	−0.0057 (18)	0.0139 (14)	−0.0020 (15)
C27A	0.052 (2)	0.032 (2)	0.040 (2)	0.005 (2)	0.0160 (19)	0.0017 (18)
C28A	0.040 (2)	0.055 (3)	0.046 (2)	−0.002 (2)	0.0107 (19)	−0.006 (2)
N1A	0.0411 (18)	0.054 (2)	0.0299 (15)	−0.0039 (18)	0.0160 (14)	0.0051 (16)
N2A	0.099 (3)	0.095 (4)	0.047 (2)	0.049 (3)	0.027 (2)	0.018 (2)
C1A	0.035 (2)	0.048 (3)	0.0354 (19)	−0.010 (2)	0.0100 (16)	0.0043 (19)
C2A	0.050 (3)	0.064 (3)	0.051 (2)	−0.001 (3)	0.026 (2)	0.006 (2)
C3A	0.056 (3)	0.070 (4)	0.070 (3)	0.003 (3)	0.030 (3)	0.007 (3)
C4A	0.049 (3)	0.054 (3)	0.064 (3)	−0.002 (2)	0.014 (2)	0.011 (3)
C5A	0.039 (2)	0.063 (3)	0.043 (2)	−0.008 (2)	0.0005 (19)	0.014 (2)
C6A	0.036 (2)	0.058 (3)	0.037 (2)	−0.014 (2)	0.0114 (17)	−0.002 (2)
C7A	0.048 (2)	0.068 (3)	0.0252 (18)	−0.011 (2)	0.0063 (17)	0.008 (2)
C8A	0.052 (2)	0.063 (3)	0.0303 (19)	0.001 (2)	0.0139 (18)	0.007 (2)
C9A	0.034 (2)	0.051 (3)	0.0316 (18)	−0.010 (2)	0.0125 (16)	−0.0017 (18)
C10A	0.044 (2)	0.053 (3)	0.0271 (18)	−0.008 (2)	0.0129 (17)	0.0007 (18)
C11A	0.044 (2)	0.059 (3)	0.0250 (17)	−0.012 (2)	0.0087 (16)	0.0010 (18)
C12A	0.041 (2)	0.048 (3)	0.0304 (18)	−0.004 (2)	0.0112 (16)	0.0003 (18)
C13A	0.051 (2)	0.059 (3)	0.0266 (18)	0.003 (2)	0.0123 (17)	0.0004 (19)
C14A	0.062 (3)	0.060 (3)	0.034 (2)	0.011 (3)	0.019 (2)	−0.001 (2)
C15A	0.057 (3)	0.056 (3)	0.039 (2)	0.006 (2)	0.013 (2)	0.003 (2)
C16A	0.058 (3)	0.057 (3)	0.0323 (19)	0.000 (2)	0.0169 (19)	0.006 (2)
C17A	0.044 (2)	0.059 (3)	0.0317 (19)	0.000 (2)	0.0153 (17)	0.001 (2)
C18A	0.087 (4)	0.068 (4)	0.055 (3)	0.025 (3)	0.020 (3)	0.024 (3)
C19A	0.077 (3)	0.093 (5)	0.048 (3)	0.008 (3)	0.021 (3)	0.033 (3)
C20A	0.061 (7)	0.045 (5)	0.051 (5)	0.011 (6)	0.008 (4)	0.007 (4)
C21A	0.089 (7)	0.055 (6)	0.069 (7)	0.016 (5)	0.013 (5)	0.000 (5)
C20X	0.054 (9)	0.038 (10)	0.051 (10)	−0.011 (8)	0.014 (7)	0.000 (8)
C21X	0.056 (12)	0.060 (12)	0.060 (10)	0.004 (9)	0.026 (8)	0.009 (8)
C22A	0.066 (3)	0.074 (4)	0.036 (2)	0.007 (3)	0.028 (2)	0.011 (2)
Cl1B	0.0747 (8)	0.0558 (8)	0.0571 (6)	0.0224 (7)	0.0284 (6)	−0.0002 (6)
S1B	0.0768 (8)	0.0564 (8)	0.0458 (6)	0.0258 (7)	0.0285 (6)	0.0085 (6)
O1B	0.069 (3)	0.111 (4)	0.102 (3)	0.033 (3)	0.059 (3)	0.043 (3)
O2B	0.122 (4)	0.082 (3)	0.048 (2)	0.061 (3)	0.020 (2)	−0.009 (2)
O3B	0.077 (3)	0.060 (3)	0.0453 (19)	0.021 (2)	0.0270 (18)	0.0125 (18)
C23B	0.055 (3)	0.038 (2)	0.0343 (19)	0.011 (2)	0.0236 (19)	0.0012 (18)
C24B	0.050 (3)	0.052 (3)	0.053 (2)	−0.004 (2)	0.019 (2)	−0.015 (2)
C25B	0.065 (3)	0.035 (2)	0.057 (3)	−0.004 (2)	0.030 (2)	−0.011 (2)
C26B	0.051 (2)	0.042 (3)	0.0334 (19)	0.003 (2)	0.0192 (18)	0.0005 (18)
C27B	0.051 (2)	0.049 (3)	0.043 (2)	−0.004 (2)	0.0179 (19)	−0.011 (2)
C28B	0.062 (3)	0.033 (2)	0.047 (2)	−0.005 (2)	0.030 (2)	−0.0081 (19)
N1B	0.050 (2)	0.045 (2)	0.049 (2)	0.0006 (19)	0.0180 (16)	−0.0041 (17)
N2B	0.111 (4)	0.154 (5)	0.045 (2)	−0.086 (4)	0.039 (2)	−0.033 (3)
C1B	0.037 (2)	0.037 (3)	0.067 (3)	0.003 (2)	0.015 (2)	0.003 (2)
C2B	0.052 (3)	0.064 (4)	0.066 (3)	0.000 (3)	0.007 (2)	−0.010 (3)
C3B	0.055 (3)	0.062 (4)	0.094 (4)	−0.006 (3)	0.006 (3)	−0.013 (3)
C4B	0.049 (3)	0.048 (3)	0.118 (5)	−0.005 (3)	0.018 (3)	−0.008 (4)
C5B	0.054 (3)	0.049 (3)	0.101 (4)	0.000 (3)	0.035 (3)	0.008 (3)
C6B	0.043 (2)	0.046 (3)	0.071 (3)	0.010 (2)	0.020 (2)	−0.005 (2)
C7B	0.067 (3)	0.058 (3)	0.065 (3)	0.003 (3)	0.038 (3)	0.006 (3)
C8B	0.063 (3)	0.047 (3)	0.057 (3)	−0.011 (2)	0.030 (2)	0.000 (2)
C9B	0.050 (2)	0.035 (2)	0.044 (2)	0.004 (2)	0.0179 (19)	−0.0065 (19)
C10B	0.052 (2)	0.042 (3)	0.043 (2)	−0.003 (2)	0.0211 (19)	0.000 (2)
C11B	0.064 (3)	0.046 (3)	0.045 (2)	−0.005 (2)	0.030 (2)	−0.002 (2)
C12B	0.055 (2)	0.039 (3)	0.045 (2)	−0.003 (2)	0.0257 (19)	−0.0014 (19)
C13B	0.073 (3)	0.063 (3)	0.044 (2)	−0.019 (3)	0.029 (2)	−0.010 (2)
C14B	0.064 (3)	0.070 (4)	0.039 (2)	−0.013 (3)	0.025 (2)	−0.009 (2)
C15B	0.066 (3)	0.084 (4)	0.042 (2)	−0.030 (3)	0.026 (2)	−0.014 (2)
C16B	0.088 (4)	0.096 (4)	0.040 (2)	−0.040 (3)	0.036 (2)	−0.018 (3)
C17B	0.063 (3)	0.057 (3)	0.040 (2)	−0.011 (3)	0.021 (2)	−0.013 (2)
C18B	0.035 (5)	0.045 (7)	0.048 (6)	−0.016 (5)	0.027 (4)	−0.013 (5)
C19B	0.091 (9)	0.045 (9)	0.036 (6)	−0.021 (7)	0.016 (7)	0.003 (5)
C18Y	0.101 (12)	0.045 (10)	0.081 (13)	−0.007 (9)	0.043 (11)	−0.007 (9)
C19Y	0.082 (10)	0.108 (11)	0.061 (7)	−0.012 (8)	0.035 (7)	0.011 (7)
C20B	0.056 (3)	0.085 (4)	0.053 (3)	−0.021 (3)	0.019 (2)	−0.020 (3)
C21B	0.072 (3)	0.073 (4)	0.068 (3)	−0.008 (3)	0.017 (3)	−0.003 (3)
C22B	0.081 (3)	0.069 (4)	0.048 (3)	−0.011 (3)	0.020 (2)	−0.003 (2)
O1WA	0.0540 (19)	0.072 (2)	0.074 (2)	0.0148 (18)	0.0227 (17)	0.0020 (19)
O1WB	0.103 (4)	0.110 (4)	0.169 (5)	0.040 (3)	0.036 (3)	0.045 (4)

Cl1A—C23A	1.745 (4)	S1B—O2B	1.430 (4)
S1A—O3A	1.446 (3)	S1B—O1B	1.481 (4)
S1A—O2A	1.449 (3)	S1B—O2Y	1.67 (5)
S1A—O1A	1.455 (3)	S1B—C26B	1.768 (4)
S1A—C26A	1.779 (4)	C23B—C24B	1.371 (6)
C23A—C24A	1.366 (6)	C23B—C28B	1.373 (6)
C23A—C28A	1.382 (6)	C24B—C25B	1.377 (6)
C24A—C25A	1.375 (6)	C24B—H24B	0.9300
C24A—H24A	0.9300	C25B—C26B	1.382 (6)
C25A—C26A	1.379 (5)	C25B—H25B	0.9300
C25A—H25A	0.9300	C26B—C27B	1.382 (6)
C26A—C27A	1.378 (5)	C27B—C28B	1.383 (6)
C27A—C28A	1.378 (6)	C27B—H27B	0.9300
C27A—H27A	0.9300	C28B—H28B	0.9300
C28A—H28A	0.9300	N1B—C9B	1.349 (5)
N1A—C9A	1.355 (5)	N1B—C1B	1.413 (6)
N1A—C1A	1.393 (5)	N1B—C22B	1.448 (5)
N1A—C22A	1.473 (5)	N2B—C15B	1.359 (6)
N2A—C15A	1.352 (6)	N2B—C18B	1.460 (13)
N2A—C18A	1.457 (6)	N2B—C20B	1.483 (6)
N2A—C20X	1.48 (2)	N2B—C18Y	1.74 (2)
N2A—C20A	1.546 (15)	C1B—C2B	1.392 (6)
C1A—C2A	1.398 (6)	C1B—C6B	1.404 (6)
C1A—C6A	1.425 (5)	C2B—C3B	1.341 (7)
C2A—C3A	1.356 (7)	C2B—H2BA	0.9300
C2A—H2AA	0.9300	C3B—C4B	1.381 (8)
C3A—C4A	1.392 (6)	C3B—H3BA	0.9300
C3A—H3AA	0.9300	C4B—C5B	1.351 (8)
C4A—C5A	1.350 (6)	C4B—H4BA	0.9300
C4A—H4AA	0.9300	C5B—C6B	1.426 (7)
C5A—C6A	1.411 (6)	C5B—H5BA	0.9300
C5A—H5AA	0.9300	C6B—C7B	1.402 (7)
C6A—C7A	1.400 (6)	C7B—C8B	1.346 (6)
C7A—C8A	1.346 (6)	C7B—H7BA	0.9300
C7A—H7AA	0.9300	C8B—C9B	1.438 (6)
C8A—C9A	1.435 (5)	C8B—H8BA	0.9300
C8A—H8AA	0.9300	C9B—C10B	1.434 (6)
C9A—C10A	1.433 (6)	C10B—C11B	1.324 (6)
C10A—C11A	1.343 (6)	C10B—H10B	0.9300
C10A—H10A	0.9300	C11B—C12B	1.445 (6)
C11A—C12A	1.442 (6)	C11B—H11B	0.9300
C11A—H11A	0.9300	C12B—C17B	1.387 (5)
C12A—C13A	1.391 (5)	C12B—C13B	1.392 (6)
C12A—C17A	1.408 (5)	C13B—C14B	1.357 (6)
C13A—C14A	1.355 (6)	C13B—H13B	0.9300
C13A—H13A	0.9300	C14B—C15B	1.403 (6)
C14A—C15A	1.416 (6)	C14B—H14B	0.9300
C14A—H14A	0.9300	C15B—C16B	1.422 (6)
C15A—C16A	1.418 (6)	C16B—C17B	1.379 (6)
C16A—C17A	1.358 (6)	C16B—H16B	0.9300
C16A—H16A	0.9300	C17B—H17B	0.9300
C17A—H17A	0.9300	C18B—C19B	1.55 (2)
C18A—C19A	1.511 (8)	C18B—H18C	0.9700
C18A—H18A	0.9700	C18B—H18D	0.9700
C18A—H18B	0.9700	C19B—H19D	0.9600
C19A—H19A	0.9600	C19B—H19E	0.9600
C19A—H19B	0.9600	C19B—H19F	0.9600
C19A—H19C	0.9600	C18Y—C19Y	1.44 (3)
C20A—C21A	1.503 (17)	C18Y—H18E	0.9700
C20A—H20A	0.9700	C18Y—H18F	0.9700
C20A—H20B	0.9700	C19Y—H19G	0.9600
C21A—H21A	0.9600	C19Y—H19H	0.9600
C21A—H21B	0.9600	C19Y—H19I	0.9600
C21A—H21C	0.9600	C20B—C21B	1.490 (7)
C20X—C21X	1.55 (3)	C20B—H20E	0.9700
C20X—H20C	0.9700	C20B—H20F	0.9700
C20X—H20D	0.9700	C21B—H21G	0.9600
C21X—H21D	0.9600	C21B—H21H	0.9600
C21X—H21E	0.9600	C21B—H21I	0.9600
C21X—H21F	0.9600	C22B—H22D	0.9600
C22A—H22A	0.9600	C22B—H22E	0.9600
C22A—H22B	0.9600	C22B—H22F	0.9600
C22A—H22C	0.9600	O1WA—H1WA	0.8388
Cl1B—C23B	1.743 (4)	O1WA—H2WA	0.7583
S1B—O1Y	1.34 (4)	O1WB—H1WB	0.8496
S1B—O3Y	1.36 (3)	O1WB—H2WB	0.8297
S1B—O3B	1.417 (3)
O3A—S1A—O2A	113.70 (18)	O2B—S1B—O1B	111.5 (3)
O3A—S1A—O1A	113.45 (19)	O1Y—S1B—O2Y	127 (2)
O2A—S1A—O1A	112.33 (18)	O3Y—S1B—O2Y	96 (2)
O3A—S1A—C26A	104.97 (16)	O3B—S1B—O2Y	49.6 (17)
O2A—S1A—C26A	105.79 (19)	O2B—S1B—O2Y	71.5 (17)
O1A—S1A—C26A	105.65 (17)	O1B—S1B—O2Y	153.8 (17)
C24A—C23A—C28A	122.1 (4)	O1Y—S1B—C26B	103.0 (16)
C24A—C23A—Cl1A	118.9 (3)	O3Y—S1B—C26B	103.8 (12)
C28A—C23A—Cl1A	119.0 (3)	O3B—S1B—C26B	106.73 (19)
C23A—C24A—C25A	118.6 (4)	O2B—S1B—C26B	106.4 (2)
C23A—C24A—H24A	120.7	O1B—S1B—C26B	105.2 (2)
C25A—C24A—H24A	120.7	O2Y—S1B—C26B	98.3 (16)
C24A—C25A—C26A	120.8 (4)	C24B—C23B—C28B	121.3 (4)
C24A—C25A—H25A	119.6	C24B—C23B—Cl1B	119.2 (3)
C26A—C25A—H25A	119.6	C28B—C23B—Cl1B	119.5 (3)
C27A—C26A—C25A	119.7 (4)	C23B—C24B—C25B	119.2 (4)
C27A—C26A—S1A	119.1 (3)	C23B—C24B—H24B	120.4
C25A—C26A—S1A	121.0 (3)	C25B—C24B—H24B	120.4
C28A—C27A—C26A	120.2 (4)	C24B—C25B—C26B	121.1 (4)
C28A—C27A—H27A	119.9	C24B—C25B—H25B	119.5
C26A—C27A—H27A	119.9	C26B—C25B—H25B	119.5
C27A—C28A—C23A	118.6 (4)	C25B—C26B—C27B	118.5 (4)
C27A—C28A—H28A	120.7	C25B—C26B—S1B	119.9 (3)
C23A—C28A—H28A	120.7	C27B—C26B—S1B	121.6 (3)
C9A—N1A—C1A	123.2 (3)	C26B—C27B—C28B	121.1 (4)
C9A—N1A—C22A	119.6 (4)	C26B—C27B—H27B	119.5
C1A—N1A—C22A	117.2 (3)	C28B—C27B—H27B	119.5
C15A—N2A—C18A	122.4 (4)	C23B—C28B—C27B	118.8 (4)
C15A—N2A—C20X	121.1 (7)	C23B—C28B—H28B	120.6
C18A—N2A—C20X	111.1 (7)	C27B—C28B—H28B	120.6
C15A—N2A—C20A	119.6 (5)	C9B—N1B—C1B	122.5 (4)
C18A—N2A—C20A	115.6 (5)	C9B—N1B—C22B	120.3 (4)
N1A—C1A—C2A	123.0 (3)	C1B—N1B—C22B	117.2 (4)
N1A—C1A—C6A	118.5 (4)	C15B—N2B—C18B	121.0 (5)
C2A—C1A—C6A	118.5 (4)	C15B—N2B—C20B	122.5 (4)
C3A—C2A—C1A	120.3 (4)	C18B—N2B—C20B	116.0 (5)
C3A—C2A—H2AA	119.9	C15B—N2B—C18Y	115.2 (7)
C1A—C2A—H2AA	119.9	C20B—N2B—C18Y	113.6 (7)
C2A—C3A—C4A	121.7 (5)	C2B—C1B—C6B	119.1 (5)
C2A—C3A—H3AA	119.2	C2B—C1B—N1B	121.9 (4)
C4A—C3A—H3AA	119.2	C6B—C1B—N1B	118.9 (4)
C5A—C4A—C3A	119.7 (5)	C3B—C2B—C1B	120.0 (5)
C5A—C4A—H4AA	120.2	C3B—C2B—H2BA	120.0
C3A—C4A—H4AA	120.2	C1B—C2B—H2BA	120.0
C4A—C5A—C6A	120.9 (4)	C2B—C3B—C4B	122.2 (6)
C4A—C5A—H5AA	119.6	C2B—C3B—H3BA	118.9
C6A—C5A—H5AA	119.6	C4B—C3B—H3BA	118.9
C7A—C6A—C5A	122.9 (4)	C5B—C4B—C3B	120.2 (5)
C7A—C6A—C1A	118.2 (4)	C5B—C4B—H4BA	119.9
C5A—C6A—C1A	118.9 (4)	C3B—C4B—H4BA	119.9
C8A—C7A—C6A	121.7 (4)	C4B—C5B—C6B	119.5 (5)
C8A—C7A—H7AA	119.2	C4B—C5B—H5BA	120.3
C6A—C7A—H7AA	119.2	C6B—C5B—H5BA	120.3
C7A—C8A—C9A	121.0 (4)	C7B—C6B—C1B	118.7 (4)
C7A—C8A—H8AA	119.5	C7B—C6B—C5B	122.2 (5)
C9A—C8A—H8AA	119.5	C1B—C6B—C5B	119.0 (5)
N1A—C9A—C10A	121.4 (3)	C8B—C7B—C6B	121.1 (4)
N1A—C9A—C8A	117.3 (4)	C8B—C7B—H7BA	119.5
C10A—C9A—C8A	121.2 (4)	C6B—C7B—H7BA	119.5
C11A—C10A—C9A	124.0 (3)	C7B—C8B—C9B	121.3 (4)
C11A—C10A—H10A	118.0	C7B—C8B—H8BA	119.3
C9A—C10A—H10A	118.0	C9B—C8B—H8BA	119.3
C10A—C11A—C12A	127.7 (3)	N1B—C9B—C10B	122.1 (4)
C10A—C11A—H11A	116.2	N1B—C9B—C8B	117.4 (4)
C12A—C11A—H11A	116.2	C10B—C9B—C8B	120.3 (4)
C13A—C12A—C17A	116.4 (4)	C11B—C10B—C9B	124.0 (4)
C13A—C12A—C11A	120.0 (3)	C11B—C10B—H10B	118.0
C17A—C12A—C11A	123.6 (4)	C9B—C10B—H10B	118.0
C14A—C13A—C12A	122.7 (4)	C10B—C11B—C12B	128.6 (4)
C14A—C13A—H13A	118.6	C10B—C11B—H11B	115.7
C12A—C13A—H13A	118.6	C12B—C11B—H11B	115.7
C13A—C14A—C15A	121.6 (4)	C17B—C12B—C13B	116.5 (4)
C13A—C14A—H14A	119.2	C17B—C12B—C11B	125.3 (4)
C15A—C14A—H14A	119.2	C13B—C12B—C11B	118.2 (4)
N2A—C15A—C14A	121.9 (4)	C14B—C13B—C12B	122.9 (4)
N2A—C15A—C16A	122.5 (4)	C14B—C13B—H13B	118.6
C14A—C15A—C16A	115.6 (4)	C12B—C13B—H13B	118.6
C17A—C16A—C15A	122.0 (4)	C13B—C14B—C15B	121.5 (4)
C17A—C16A—H16A	119.0	C13B—C14B—H14B	119.2
C15A—C16A—H16A	119.0	C15B—C14B—H14B	119.2
C16A—C17A—C12A	121.7 (4)	N2B—C15B—C14B	121.1 (4)
C16A—C17A—H17A	119.2	N2B—C15B—C16B	122.8 (4)
C12A—C17A—H17A	119.2	C14B—C15B—C16B	116.1 (4)
N2A—C18A—C19A	112.6 (5)	C17B—C16B—C15B	120.9 (4)
N2A—C18A—H18A	109.1	C17B—C16B—H16B	119.6
C19A—C18A—H18A	109.1	C15B—C16B—H16B	119.6
N2A—C18A—H18B	109.1	C16B—C17B—C12B	122.1 (4)
C19A—C18A—H18B	109.1	C16B—C17B—H17B	118.9
H18A—C18A—H18B	107.8	C12B—C17B—H17B	118.9
C18A—C19A—H19A	109.5	N2B—C18B—C19B	104.4 (10)
C18A—C19A—H19B	109.5	N2B—C18B—H18C	110.9
H19A—C19A—H19B	109.5	C19B—C18B—H18C	110.9
C18A—C19A—H19C	109.5	N2B—C18B—H18D	110.9
H19A—C19A—H19C	109.5	C19B—C18B—H18D	110.9
H19B—C19A—H19C	109.5	H18C—C18B—H18D	108.9
C21A—C20A—N2A	106.3 (12)	C19Y—C18Y—N2B	94.1 (15)
C21A—C20A—H20A	110.5	C19Y—C18Y—H18E	112.9
N2A—C20A—H20A	110.5	N2B—C18Y—H18E	112.9
C21A—C20A—H20B	110.5	C19Y—C18Y—H18F	112.9
N2A—C20A—H20B	110.5	N2B—C18Y—H18F	112.9
H20A—C20A—H20B	108.7	H18E—C18Y—H18F	110.3
N2A—C20X—C21X	99.4 (16)	C18Y—C19Y—H19G	109.5
N2A—C20X—H20C	111.9	C18Y—C19Y—H19H	109.5
C21X—C20X—H20C	111.9	H19G—C19Y—H19H	109.5
N2A—C20X—H20D	111.9	C18Y—C19Y—H19I	109.5
C21X—C20X—H20D	111.9	H19G—C19Y—H19I	109.5
H20C—C20X—H20D	109.6	H19H—C19Y—H19I	109.5
C20X—C21X—H21D	109.5	N2B—C20B—C21B	112.8 (5)
C20X—C21X—H21E	109.5	N2B—C20B—H20E	109.0
H21D—C21X—H21E	109.5	C21B—C20B—H20E	109.0
C20X—C21X—H21F	109.5	N2B—C20B—H20F	109.0
H21D—C21X—H21F	109.5	C21B—C20B—H20F	109.0
H21E—C21X—H21F	109.5	H20E—C20B—H20F	107.8
N1A—C22A—H22A	109.5	C20B—C21B—H21G	109.5
N1A—C22A—H22B	109.5	C20B—C21B—H21H	109.5
H22A—C22A—H22B	109.5	H21G—C21B—H21H	109.5
N1A—C22A—H22C	109.5	C20B—C21B—H21I	109.5
H22A—C22A—H22C	109.5	H21G—C21B—H21I	109.5
H22B—C22A—H22C	109.5	H21H—C21B—H21I	109.5
O1Y—S1B—O3Y	123 (2)	N1B—C22B—H22D	109.5
O1Y—S1B—O3B	150.2 (16)	N1B—C22B—H22E	109.5
O3Y—S1B—O3B	46.8 (13)	H22D—C22B—H22E	109.5
O1Y—S1B—O2B	56.5 (18)	N1B—C22B—H22F	109.5
O3Y—S1B—O2B	148.7 (12)	H22D—C22B—H22F	109.5
O3B—S1B—O2B	115.0 (3)	H22E—C22B—H22F	109.5
O1Y—S1B—O1B	58.0 (18)	H1WA—O1WA—H2WA	110.0
O3Y—S1B—O1B	67.2 (13)	H1WB—O1WB—H2WB	107.8
O3B—S1B—O1B	111.2 (3)
C28A—C23A—C24A—C25A	−0.4 (5)	C24B—C25B—C26B—C27B	0.6 (6)
Cl1A—C23A—C24A—C25A	179.1 (3)	C24B—C25B—C26B—S1B	−179.5 (3)
C23A—C24A—C25A—C26A	0.2 (5)	O1Y—S1B—C26B—C25B	−88.0 (19)
C24A—C25A—C26A—C27A	−0.3 (5)	O3Y—S1B—C26B—C25B	142.4 (14)
C24A—C25A—C26A—S1A	−176.7 (3)	O3B—S1B—C26B—C25B	93.9 (4)
O3A—S1A—C26A—C27A	−83.0 (3)	O2B—S1B—C26B—C25B	−29.4 (4)
O2A—S1A—C26A—C27A	156.5 (3)	O1B—S1B—C26B—C25B	−147.9 (4)
O1A—S1A—C26A—C27A	37.2 (3)	O2Y—S1B—C26B—C25B	43.6 (18)
O3A—S1A—C26A—C25A	93.5 (3)	O1Y—S1B—C26B—C27B	91.9 (19)
O2A—S1A—C26A—C25A	−27.0 (3)	O3Y—S1B—C26B—C27B	−37.7 (14)
O1A—S1A—C26A—C25A	−146.3 (3)	O3B—S1B—C26B—C27B	−86.3 (4)
C25A—C26A—C27A—C28A	0.5 (5)	O2B—S1B—C26B—C27B	150.4 (4)
S1A—C26A—C27A—C28A	177.0 (3)	O1B—S1B—C26B—C27B	32.0 (4)
C26A—C27A—C28A—C23A	−0.6 (6)	O2Y—S1B—C26B—C27B	−136.5 (18)
C24A—C23A—C28A—C27A	0.6 (6)	C25B—C26B—C27B—C28B	−0.6 (6)
Cl1A—C23A—C28A—C27A	−178.9 (3)	S1B—C26B—C27B—C28B	179.6 (3)
C9A—N1A—C1A—C2A	−173.2 (4)	C24B—C23B—C28B—C27B	0.9 (6)
C22A—N1A—C1A—C2A	8.1 (6)	Cl1B—C23B—C28B—C27B	−179.3 (3)
C9A—N1A—C1A—C6A	5.0 (6)	C26B—C27B—C28B—C23B	−0.1 (6)
C22A—N1A—C1A—C6A	−173.7 (4)	C9B—N1B—C1B—C2B	175.6 (4)
N1A—C1A—C2A—C3A	−179.7 (4)	C22B—N1B—C1B—C2B	−4.9 (6)
C6A—C1A—C2A—C3A	2.1 (6)	C9B—N1B—C1B—C6B	−1.8 (6)
C1A—C2A—C3A—C4A	−0.1 (7)	C22B—N1B—C1B—C6B	177.7 (4)
C2A—C3A—C4A—C5A	−2.0 (7)	C6B—C1B—C2B—C3B	−1.6 (7)
C3A—C4A—C5A—C6A	2.0 (7)	N1B—C1B—C2B—C3B	−179.1 (4)
C4A—C5A—C6A—C7A	−176.9 (4)	C1B—C2B—C3B—C4B	0.5 (8)
C4A—C5A—C6A—C1A	−0.1 (6)	C2B—C3B—C4B—C5B	0.3 (8)
N1A—C1A—C6A—C7A	−3.2 (6)	C3B—C4B—C5B—C6B	0.0 (8)
C2A—C1A—C6A—C7A	175.0 (4)	C2B—C1B—C6B—C7B	−176.7 (4)
N1A—C1A—C6A—C5A	179.8 (4)	N1B—C1B—C6B—C7B	0.9 (6)
C2A—C1A—C6A—C5A	−1.9 (6)	C2B—C1B—C6B—C5B	1.9 (6)
C5A—C6A—C7A—C8A	177.2 (4)	N1B—C1B—C6B—C5B	179.5 (4)
C1A—C6A—C7A—C8A	0.3 (6)	C4B—C5B—C6B—C7B	177.4 (5)
C6A—C7A—C8A—C9A	1.1 (7)	C4B—C5B—C6B—C1B	−1.1 (7)
C1A—N1A—C9A—C10A	173.3 (4)	C1B—C6B—C7B—C8B	0.3 (7)
C22A—N1A—C9A—C10A	−8.0 (6)	C5B—C6B—C7B—C8B	−178.3 (4)
C1A—N1A—C9A—C8A	−3.6 (6)	C6B—C7B—C8B—C9B	−0.6 (7)
C22A—N1A—C9A—C8A	175.2 (4)	C1B—N1B—C9B—C10B	−173.2 (4)
C7A—C8A—C9A—N1A	0.4 (6)	C22B—N1B—C9B—C10B	7.3 (6)
C7A—C8A—C9A—C10A	−176.5 (4)	C1B—N1B—C9B—C8B	1.5 (6)
N1A—C9A—C10A—C11A	179.4 (4)	C22B—N1B—C9B—C8B	−178.0 (4)
C8A—C9A—C10A—C11A	−3.8 (6)	C7B—C8B—C9B—N1B	−0.3 (7)
C9A—C10A—C11A—C12A	174.6 (4)	C7B—C8B—C9B—C10B	174.5 (4)
C10A—C11A—C12A—C13A	−173.0 (4)	N1B—C9B—C10B—C11B	175.8 (4)
C10A—C11A—C12A—C17A	5.6 (7)	C8B—C9B—C10B—C11B	1.3 (7)
C17A—C12A—C13A—C14A	−0.7 (6)	C9B—C10B—C11B—C12B	−172.5 (4)
C11A—C12A—C13A—C14A	178.0 (4)	C10B—C11B—C12B—C17B	−4.1 (8)
C12A—C13A—C14A—C15A	1.7 (7)	C10B—C11B—C12B—C13B	173.9 (5)
C18A—N2A—C15A—C14A	−178.5 (5)	C17B—C12B—C13B—C14B	0.7 (7)
C20X—N2A—C15A—C14A	−26.7 (11)	C11B—C12B—C13B—C14B	−177.5 (5)
C20A—N2A—C15A—C14A	20.0 (9)	C12B—C13B—C14B—C15B	0.1 (8)
C18A—N2A—C15A—C16A	3.2 (8)	C18B—N2B—C15B—C14B	−168.8 (7)
C20X—N2A—C15A—C16A	154.9 (8)	C20B—N2B—C15B—C14B	2.7 (9)
C20A—N2A—C15A—C16A	−158.4 (6)	C18Y—N2B—C15B—C14B	148.1 (8)
C13A—C14A—C15A—N2A	−179.8 (5)	C18B—N2B—C15B—C16B	10.1 (11)
C13A—C14A—C15A—C16A	−1.3 (7)	C20B—N2B—C15B—C16B	−178.5 (6)
N2A—C15A—C16A—C17A	178.6 (5)	C18Y—N2B—C15B—C16B	−33.1 (10)
C14A—C15A—C16A—C17A	0.1 (7)	C13B—C14B—C15B—N2B	177.6 (6)
C15A—C16A—C17A—C12A	0.8 (7)	C13B—C14B—C15B—C16B	−1.4 (8)
C13A—C12A—C17A—C16A	−0.5 (6)	N2B—C15B—C16B—C17B	−177.1 (6)
C11A—C12A—C17A—C16A	−179.1 (4)	C14B—C15B—C16B—C17B	1.8 (8)
C15A—N2A—C18A—C19A	−84.1 (7)	C15B—C16B—C17B—C12B	−1.1 (8)
C20X—N2A—C18A—C19A	121.6 (8)	C13B—C12B—C17B—C16B	−0.2 (7)
C20A—N2A—C18A—C19A	78.1 (7)	C11B—C12B—C17B—C16B	177.9 (5)
C15A—N2A—C20A—C21A	−96.3 (8)	C15B—N2B—C18B—C19B	−83.7 (10)
C18A—N2A—C20A—C21A	100.9 (7)	C20B—N2B—C18B—C19B	104.4 (8)
C20X—N2A—C20A—C21A	8.0 (10)	C18Y—N2B—C18B—C19B	8.6 (14)
C15A—N2A—C20X—C21X	100.0 (11)	C15B—N2B—C18Y—C19Y	112.6 (10)
C18A—N2A—C20X—C21X	−105.4 (10)	C18B—N2B—C18Y—C19Y	3.8 (8)
C20A—N2A—C20X—C21X	−0.3 (10)	C20B—N2B—C18Y—C19Y	−98.9 (10)
C28B—C23B—C24B—C25B	−0.8 (6)	C15B—N2B—C20B—C21B	79.0 (8)
Cl1B—C23B—C24B—C25B	179.3 (3)	C18B—N2B—C20B—C21B	−109.2 (7)
C23B—C24B—C25B—C26B	0.1 (6)	C18Y—N2B—C20B—C21B	−66.9 (9)

D—H···A	D—H	H···A	D···A	D—H···A
O1WB—H1WB···O1Bi	0.85	2.36	2.815 (7)	114
O1WB—H2WB···O2Bii	0.83	2.12	2.953 (7)	177
O1WA—H1WA···O2Aiii	0.84	2.07	2.891 (5)	166
O1WA—H2WA···O1A	0.76	2.10	2.844 (4)	169
C8A—H8AA···O3Aiv	0.93	2.54	3.146 (5)	123
C2B—H2BA···O3Bv	0.93	2.57	3.314 (7)	137
C11B—H11B···O1Bvi	0.93	2.41	3.237 (6)	148
C18Y—H18E···Cl1Avii	0.97	2.72	3.673 (19)	169
C19B—H19D···Cl1Bviii	0.96	2.73	3.531 (14)	142
C22B—H22D···O2Bviii	0.96	2.55	3.259 (7)	131
C25A—H25A···O3Aii	0.93	2.56	3.359 (5)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1WB—H1WB⋯O1B i	0.85	2.36	2.815 (7)	114
O1WB—H2WB⋯O2B ii	0.83	2.12	2.953 (7)	177
O1WA—H1WA⋯O2A iii	0.84	2.07	2.891 (5)	166
O1WA—H2WA⋯O1A	0.76	2.10	2.844 (4)	169
C8A—H8AA⋯O3A iv	0.93	2.54	3.146 (5)	123
C2B—H2BA⋯O3B v	0.93	2.57	3.314 (7)	137
C11B—H11B⋯O1B vi	0.93	2.41	3.237 (6)	148
C18Y—H18E⋯Cl1A vii	0.97	2.72	3.673 (19)	169
C19B—H19D⋯Cl1B viii	0.96	2.73	3.531 (14)	142
C22B—H22D⋯O2B viii	0.96	2.55	3.259 (7)	131
C25A—H25A⋯O3A ii	0.93	2.56	3.359 (5)	144

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) .