Bis[4-(4-chloro-phen-yl)-4-hydroxy-piperidinium] dipicrate dimethyl sulfoxide solvate.

The asymmetric unit of the title salt solvate, 2C(11)H(15)ClNO(+)·2C(6)H(2)N(3)O(7) (-)·C(2)H(6)OS, contains two crystallographically independent 4-(4-chloro-phen-yl)-4-hydroxy-piperidinium cations, two picrate anions and a dimethyl sulfoxide solvent mol-ecule. In each cation, the piperidinium ring adopts a chair conformation. In the crystal structure, the cations, anions and solvent mol-ecules are connected by inter-molecular O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For background to the importance of piperidines, see: Vartanyan (1984 ▶). For related structures, see: Cygler et al. (1980 ▶); Cygler & Ahmed (1984 ▶); Dutkiewicz et al. (2010 ▶); Georges et al. (1989 ▶); Jasinski et al. (2009 ▶); Lisgarten & Palmer (1989 ▶); Tomlin et al. (1996 ▶). For picrate salts, see: Anitha et al. (2004 ▶); Thanigaimani et al. (2009 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

2C11H15ClNO+·2C6H2N3O7 −·C2H6OS

M = 959.72

Monoclinic,

a = 8.9207 (4) Å

b = 18.1230 (9) Å

c = 12.9886 (6) Å

β = 98.430 (1)°

V = 2077.18 (17) Å3

Z = 2

Mo Kα radiation

μ = 0.29 mm−1

T = 100 K

0.40 × 0.32 × 0.16 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.893, T max = 0.954

25314 measured reflections

15185 independent reflections

13604 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.140

S = 1.11

15185 reflections

582 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.83 e Å−3

Δρmin = −0.88 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810015187/tk2662sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015187/tk2662Isup2.hkl

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

2C11H15ClNO+·2C6H2N3O7−·C2H6OS	F(000) = 996
Mr = 959.72	Dx = 1.533 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 9240 reflections
a = 8.9207 (4) Å	θ = 2.6–34.7°
b = 18.1230 (9) Å	µ = 0.29 mm−1
c = 12.9886 (6) Å	T = 100 K
β = 98.430 (1)°	Block, yellow
V = 2077.18 (17) Å3	0.40 × 0.32 × 0.16 mm
Z = 2

Bruker APEX DUO CCD area-detector diffractometer	15185 independent reflections
Radiation source: fine-focus sealed tube	13604 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 34.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→11
Tmin = 0.893, Tmax = 0.954	k = −25→28
25314 measured reflections	l = −20→20

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0893P)2] where P = (Fo2 + 2Fc2)/3
15185 reflections	(Δ/σ)max < 0.001
582 parameters	Δρmax = 0.83 e Å−3
1 restraint	Δρmin = −0.88 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 s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Cl1A	0.54080 (6)	0.78062 (3)	0.70106 (3)	0.01956 (9)
O1A	0.61893 (15)	1.07386 (8)	0.41761 (10)	0.0143 (2)
H1A	0.6671	1.0721	0.4764	0.021*
N1A	0.66742 (19)	1.05337 (9)	0.15938 (12)	0.0154 (3)
H1AB	0.6807	1.0893	0.1137	0.019*
H1AC	0.6638	1.0100	0.1254	0.019*
C1A	0.4866 (2)	0.89223 (11)	0.43262 (14)	0.0162 (3)
H1AA	0.4188	0.8926	0.3710	0.019*
C2A	0.4670 (2)	0.84096 (12)	0.51056 (15)	0.0175 (3)
H2AA	0.3869	0.8076	0.5012	0.021*
C3A	0.5690 (2)	0.84107 (11)	0.60158 (14)	0.0141 (3)
C4A	0.6917 (2)	0.88914 (12)	0.61605 (14)	0.0176 (3)
H4AA	0.7609	0.8877	0.6770	0.021*
C5A	0.7090 (2)	0.93908 (11)	0.53828 (14)	0.0167 (3)
H5AA	0.7911	0.9712	0.5475	0.020*
C6A	0.60617 (19)	0.94264 (11)	0.44600 (13)	0.0124 (3)
C7A	0.62592 (19)	1.00352 (10)	0.36771 (13)	0.0112 (3)
C8A	0.77725 (19)	0.99468 (11)	0.32607 (14)	0.0139 (3)
H8AA	0.8595	0.9978	0.3837	0.017*
H8AB	0.7810	0.9462	0.2949	0.017*
C9A	0.8002 (2)	1.05298 (11)	0.24570 (14)	0.0154 (3)
H9AA	0.8103	1.1011	0.2786	0.019*
H9AB	0.8926	1.0427	0.2172	0.019*
C10A	0.5206 (2)	1.06552 (12)	0.19942 (14)	0.0154 (3)
H10A	0.4379	1.0655	0.1419	0.018*
H10B	0.5221	1.1130	0.2339	0.018*
C11A	0.4964 (2)	1.00446 (11)	0.27584 (13)	0.0138 (3)
H11A	0.4916	0.9572	0.2405	0.017*
H11B	0.4008	1.0122	0.3015	0.017*
Cl1B	0.08958 (5)	0.91889 (3)	0.68165 (4)	0.02007 (9)
O1B	0.13549 (15)	0.60441 (8)	0.41992 (10)	0.0136 (2)
H1B	0.0543	0.5928	0.4378	0.020*
N1B	0.14188 (19)	0.62391 (10)	0.15802 (12)	0.0149 (3)
H1BB	0.1508	0.5882	0.1111	0.018*
H1BC	0.1357	0.6675	0.1245	0.018*
C1B	0.1208 (2)	0.72111 (11)	0.55239 (14)	0.0171 (3)
H1BA	0.1357	0.6727	0.5755	0.020*
C2B	0.1142 (2)	0.77734 (12)	0.62472 (14)	0.0179 (3)
H2BA	0.1244	0.7667	0.6954	0.022*
C3B	0.0925 (2)	0.84893 (11)	0.59017 (14)	0.0149 (3)
C4B	0.0750 (2)	0.86606 (11)	0.48428 (14)	0.0161 (3)
H4BA	0.0601	0.9146	0.4617	0.019*
C5B	0.0803 (2)	0.80906 (11)	0.41349 (14)	0.0148 (3)
H5BA	0.0669	0.8197	0.3427	0.018*
C6B	0.10545 (19)	0.73598 (10)	0.44641 (13)	0.0118 (3)
C7B	0.12034 (19)	0.67426 (10)	0.36860 (13)	0.0117 (3)
C8B	0.2656 (2)	0.68375 (11)	0.31946 (14)	0.0141 (3)
H8BA	0.2647	0.7318	0.2864	0.017*
H8BB	0.3529	0.6817	0.3735	0.017*
C9B	0.2793 (2)	0.62363 (11)	0.23875 (15)	0.0160 (3)
H9BA	0.3688	0.6323	0.2062	0.019*
H9BB	0.2898	0.5758	0.2727	0.019*
C10B	0.0000 (2)	0.61169 (11)	0.20400 (14)	0.0147 (3)
H10C	0.0040	0.5639	0.2380	0.018*
H10D	−0.0866	0.6120	0.1493	0.018*
C11B	−0.0179 (2)	0.67201 (11)	0.28259 (14)	0.0133 (3)
H11C	−0.1088	0.6630	0.3135	0.016*
H11D	−0.0290	0.7194	0.2474	0.016*
O2A	0.61771 (16)	0.91428 (8)	0.08706 (11)	0.0167 (2)
O3A	0.7941 (2)	0.99873 (9)	−0.01439 (12)	0.0238 (3)
O4A	0.8540 (2)	0.95285 (9)	−0.15570 (12)	0.0232 (3)
O5A	0.9570 (2)	0.69858 (10)	−0.17516 (15)	0.0323 (4)
O6A	0.8761 (2)	0.62139 (10)	−0.06713 (16)	0.0306 (4)
O7A	0.6214 (2)	0.71007 (10)	0.20625 (14)	0.0265 (3)
O8A	0.47444 (18)	0.80551 (10)	0.17469 (13)	0.0243 (3)
N2A	0.80695 (19)	0.94537 (9)	−0.07213 (12)	0.0148 (3)
N3A	0.8834 (2)	0.68406 (10)	−0.10369 (15)	0.0206 (3)
N4A	0.57910 (18)	0.76640 (10)	0.15561 (13)	0.0162 (3)
C12A	0.67605 (19)	0.86314 (10)	0.04248 (13)	0.0125 (3)
C13A	0.76790 (19)	0.87243 (10)	−0.04033 (13)	0.0123 (3)
C14A	0.8299 (2)	0.81494 (10)	−0.09002 (13)	0.0131 (3)
H14A	0.8853	0.8242	−0.1440	0.016*
C15A	0.8079 (2)	0.74346 (11)	−0.05797 (14)	0.0145 (3)
C16A	0.7243 (2)	0.72826 (11)	0.02189 (14)	0.0147 (3)
H16A	0.7119	0.6799	0.0430	0.018*
C17A	0.66026 (19)	0.78560 (11)	0.06925 (13)	0.0132 (3)
O2B	0.11214 (17)	0.76690 (8)	0.09635 (11)	0.0175 (3)
O3B	−0.03236 (16)	0.88222 (9)	0.17146 (11)	0.0191 (3)
O4B	0.1375 (2)	0.96634 (11)	0.21473 (14)	0.0286 (4)
O5B	0.3832 (2)	1.05229 (9)	−0.07138 (16)	0.0295 (4)
O6B	0.47519 (19)	0.97024 (9)	−0.16764 (13)	0.0230 (3)
O7B	0.3277 (2)	0.72048 (9)	−0.15469 (13)	0.0277 (4)
O8B	0.2714 (3)	0.67703 (10)	−0.01198 (14)	0.0320 (4)
N2B	0.08429 (17)	0.91522 (10)	0.15888 (12)	0.0145 (3)
N3B	0.39467 (19)	0.98818 (10)	−0.10184 (13)	0.0170 (3)
N4B	0.2868 (2)	0.72954 (10)	−0.06939 (12)	0.0157 (3)
C12B	0.17235 (19)	0.81592 (10)	0.04862 (13)	0.0127 (3)
C13B	0.16278 (19)	0.89373 (11)	0.07279 (13)	0.0123 (3)
C14B	0.23231 (19)	0.94922 (11)	0.02524 (14)	0.0141 (3)
H14B	0.2259	0.9979	0.0466	0.017*
C15B	0.3126 (2)	0.93112 (10)	−0.05568 (14)	0.0135 (3)
C16B	0.32577 (19)	0.85917 (11)	−0.08763 (13)	0.0135 (3)
H16B	0.3788	0.8480	−0.1422	0.016*
C17B	0.2583 (2)	0.80354 (10)	−0.03668 (14)	0.0129 (3)
S1	0.74330 (6)	0.56505 (3)	0.52501 (4)	0.02135 (10)
O9	0.90638 (17)	0.55756 (10)	0.50845 (13)	0.0231 (3)
C18	0.7073 (3)	0.66185 (18)	0.5327 (3)	0.0446 (8)
H18A	0.7794	0.6834	0.5865	0.067*
H18B	0.6067	0.6694	0.5486	0.067*
H18C	0.7166	0.6847	0.4672	0.067*
C19	0.6293 (2)	0.54900 (15)	0.40268 (18)	0.0258 (4)
H19A	0.6479	0.5001	0.3791	0.039*
H19B	0.6544	0.5844	0.3529	0.039*
H19C	0.5243	0.5539	0.4101	0.039*

	U11	U22	U33	U12	U13	U23
Cl1A	0.0259 (2)	0.0181 (2)	0.01581 (17)	−0.00290 (17)	0.00703 (15)	0.00415 (16)
O1A	0.0171 (5)	0.0120 (6)	0.0136 (5)	−0.0012 (4)	0.0020 (4)	−0.0027 (4)
N1A	0.0225 (7)	0.0125 (7)	0.0123 (6)	−0.0006 (5)	0.0061 (5)	0.0002 (5)
C1A	0.0156 (7)	0.0174 (8)	0.0153 (7)	−0.0051 (6)	0.0016 (6)	0.0013 (6)
C2A	0.0166 (7)	0.0186 (9)	0.0172 (7)	−0.0067 (6)	0.0023 (6)	0.0021 (6)
C3A	0.0172 (7)	0.0135 (8)	0.0124 (6)	−0.0003 (6)	0.0050 (5)	0.0022 (6)
C4A	0.0206 (7)	0.0175 (9)	0.0139 (7)	−0.0032 (6)	−0.0008 (6)	0.0015 (6)
C5A	0.0171 (7)	0.0152 (8)	0.0167 (7)	−0.0053 (6)	−0.0006 (6)	0.0019 (6)
C6A	0.0132 (6)	0.0120 (7)	0.0125 (6)	−0.0017 (5)	0.0033 (5)	−0.0002 (6)
C7A	0.0123 (6)	0.0090 (7)	0.0123 (6)	−0.0007 (5)	0.0023 (5)	−0.0013 (5)
C8A	0.0144 (7)	0.0126 (8)	0.0154 (7)	0.0006 (6)	0.0044 (5)	0.0013 (6)
C9A	0.0163 (7)	0.0142 (8)	0.0170 (7)	−0.0014 (6)	0.0065 (6)	−0.0006 (6)
C10A	0.0186 (7)	0.0140 (8)	0.0137 (7)	0.0006 (6)	0.0031 (6)	0.0011 (6)
C11A	0.0147 (6)	0.0145 (8)	0.0121 (6)	−0.0021 (6)	0.0016 (5)	−0.0006 (6)
Cl1B	0.02299 (19)	0.0197 (2)	0.01767 (18)	0.00048 (16)	0.00359 (15)	−0.00778 (16)
O1B	0.0165 (5)	0.0100 (6)	0.0146 (5)	0.0016 (4)	0.0036 (4)	0.0029 (4)
N1B	0.0226 (7)	0.0115 (7)	0.0120 (6)	−0.0004 (5)	0.0069 (5)	−0.0014 (5)
C1B	0.0264 (8)	0.0142 (8)	0.0107 (6)	0.0005 (6)	0.0032 (6)	0.0010 (6)
C2B	0.0252 (8)	0.0173 (9)	0.0118 (7)	0.0010 (7)	0.0043 (6)	−0.0001 (6)
C3B	0.0157 (7)	0.0147 (8)	0.0146 (7)	−0.0004 (6)	0.0030 (5)	−0.0041 (6)
C4B	0.0197 (7)	0.0131 (8)	0.0153 (7)	0.0027 (6)	0.0015 (6)	−0.0001 (6)
C5B	0.0195 (7)	0.0133 (8)	0.0116 (6)	0.0029 (6)	0.0018 (6)	0.0011 (6)
C6B	0.0131 (6)	0.0113 (7)	0.0109 (6)	0.0006 (5)	0.0020 (5)	0.0003 (5)
C7B	0.0144 (6)	0.0096 (7)	0.0112 (6)	0.0003 (5)	0.0026 (5)	0.0012 (5)
C8B	0.0143 (6)	0.0129 (8)	0.0158 (7)	−0.0001 (6)	0.0051 (6)	−0.0005 (6)
C9B	0.0176 (7)	0.0151 (8)	0.0170 (7)	0.0005 (6)	0.0079 (6)	−0.0010 (6)
C10B	0.0177 (7)	0.0141 (8)	0.0123 (6)	−0.0020 (6)	0.0026 (5)	−0.0003 (6)
C11B	0.0141 (7)	0.0118 (8)	0.0138 (7)	0.0000 (6)	0.0011 (5)	−0.0005 (6)
O2A	0.0194 (6)	0.0141 (6)	0.0181 (6)	−0.0003 (5)	0.0073 (5)	−0.0033 (5)
O3A	0.0447 (9)	0.0107 (7)	0.0189 (6)	−0.0030 (6)	0.0144 (6)	−0.0030 (5)
O4A	0.0412 (9)	0.0140 (7)	0.0179 (6)	−0.0003 (6)	0.0166 (6)	0.0008 (5)
O5A	0.0469 (11)	0.0186 (8)	0.0383 (9)	0.0048 (7)	0.0293 (9)	0.0016 (7)
O6A	0.0434 (10)	0.0113 (7)	0.0423 (10)	0.0027 (7)	0.0233 (8)	0.0029 (7)
O7A	0.0287 (7)	0.0238 (8)	0.0286 (8)	0.0038 (6)	0.0097 (6)	0.0132 (6)
O8A	0.0204 (6)	0.0275 (8)	0.0269 (7)	0.0030 (6)	0.0104 (6)	0.0050 (6)
N2A	0.0209 (7)	0.0109 (7)	0.0129 (6)	0.0001 (5)	0.0040 (5)	0.0013 (5)
N3A	0.0262 (8)	0.0112 (8)	0.0273 (8)	0.0017 (6)	0.0134 (7)	0.0002 (6)
N4A	0.0150 (6)	0.0165 (8)	0.0172 (7)	−0.0035 (5)	0.0030 (5)	0.0021 (5)
C12A	0.0131 (6)	0.0126 (8)	0.0119 (6)	−0.0006 (5)	0.0017 (5)	−0.0007 (6)
C13A	0.0160 (7)	0.0082 (7)	0.0126 (6)	0.0006 (5)	0.0021 (5)	0.0008 (5)
C14A	0.0160 (7)	0.0121 (8)	0.0117 (6)	0.0000 (6)	0.0036 (5)	0.0000 (6)
C15A	0.0174 (7)	0.0098 (8)	0.0169 (7)	0.0007 (6)	0.0047 (6)	−0.0012 (6)
C16A	0.0154 (7)	0.0111 (8)	0.0178 (7)	−0.0008 (6)	0.0034 (6)	0.0019 (6)
C17A	0.0135 (6)	0.0128 (8)	0.0136 (6)	−0.0008 (6)	0.0028 (5)	0.0019 (6)
O2B	0.0205 (6)	0.0141 (7)	0.0196 (6)	0.0002 (5)	0.0090 (5)	0.0018 (5)
O3B	0.0157 (5)	0.0243 (8)	0.0185 (6)	−0.0011 (5)	0.0065 (5)	−0.0018 (5)
O4B	0.0245 (7)	0.0317 (10)	0.0308 (8)	−0.0068 (6)	0.0081 (6)	−0.0191 (7)
O5B	0.0408 (9)	0.0094 (7)	0.0430 (10)	−0.0026 (6)	0.0213 (8)	−0.0013 (6)
O6B	0.0284 (7)	0.0187 (7)	0.0247 (7)	−0.0026 (6)	0.0131 (6)	0.0006 (6)
O7B	0.0472 (10)	0.0157 (7)	0.0261 (7)	−0.0023 (7)	0.0250 (7)	−0.0028 (6)
O8B	0.0656 (13)	0.0120 (7)	0.0245 (7)	0.0037 (7)	0.0269 (8)	0.0035 (6)
N2B	0.0133 (6)	0.0169 (8)	0.0133 (6)	0.0024 (5)	0.0014 (5)	−0.0020 (6)
N3B	0.0186 (6)	0.0126 (7)	0.0208 (7)	−0.0013 (5)	0.0058 (5)	0.0025 (6)
N4B	0.0240 (7)	0.0115 (7)	0.0122 (6)	−0.0007 (5)	0.0050 (5)	0.0003 (5)
C12B	0.0139 (6)	0.0122 (8)	0.0119 (6)	0.0006 (5)	0.0016 (5)	−0.0004 (6)
C13B	0.0121 (6)	0.0128 (7)	0.0123 (6)	0.0015 (5)	0.0025 (5)	−0.0007 (6)
C14B	0.0136 (6)	0.0121 (8)	0.0167 (7)	0.0010 (5)	0.0022 (6)	0.0003 (6)
C15B	0.0144 (6)	0.0106 (8)	0.0157 (7)	−0.0005 (5)	0.0032 (5)	0.0015 (6)
C16B	0.0152 (7)	0.0125 (8)	0.0128 (7)	0.0005 (6)	0.0024 (5)	0.0013 (6)
C17B	0.0165 (7)	0.0097 (7)	0.0130 (7)	0.0010 (6)	0.0035 (5)	−0.0004 (5)
S1	0.01909 (19)	0.0257 (3)	0.0210 (2)	−0.00352 (17)	0.00883 (16)	0.00180 (18)
O9	0.0174 (6)	0.0231 (8)	0.0303 (7)	−0.0003 (5)	0.0083 (5)	0.0068 (6)
C18	0.0301 (12)	0.0316 (15)	0.077 (2)	−0.0032 (10)	0.0228 (13)	−0.0224 (15)
C19	0.0195 (8)	0.0338 (13)	0.0250 (9)	0.0008 (8)	0.0064 (7)	0.0009 (8)

Cl1A—C3A	1.7402 (18)	C9B—H9BA	0.9700
O1A—C7A	1.436 (2)	C9B—H9BB	0.9700
O1A—H1A	0.8200	C10B—C11B	1.520 (3)
N1A—C10A	1.495 (2)	C10B—H10C	0.9700
N1A—C9A	1.507 (2)	C10B—H10D	0.9700
N1A—H1AB	0.9000	C11B—H11C	0.9700
N1A—H1AC	0.9000	C11B—H11D	0.9700
C1A—C6A	1.396 (2)	O2A—C12A	1.246 (2)
C1A—C2A	1.404 (3)	O3A—N2A	1.239 (2)
C1A—H1AA	0.9300	O4A—N2A	1.227 (2)
C2A—C3A	1.383 (3)	O5A—N3A	1.241 (2)
C2A—H2AA	0.9300	O6A—N3A	1.236 (2)
C3A—C4A	1.390 (3)	O7A—N4A	1.243 (2)
C4A—C5A	1.382 (3)	O8A—N4A	1.226 (2)
C4A—H4AA	0.9300	N2A—C13A	1.443 (3)
C5A—C6A	1.400 (2)	N3A—C15A	1.443 (3)
C5A—H5AA	0.9300	N4A—C17A	1.463 (2)
C6A—C7A	1.528 (2)	C12A—C13A	1.454 (2)
C7A—C8A	1.534 (2)	C12A—C17A	1.459 (3)
C7A—C11A	1.535 (2)	C13A—C14A	1.383 (3)
C8A—C9A	1.520 (3)	C14A—C15A	1.383 (3)
C8A—H8AA	0.9700	C14A—H14A	0.9300
C8A—H8AB	0.9700	C15A—C16A	1.391 (3)
C9A—H9AA	0.9700	C16A—C17A	1.374 (3)
C9A—H9AB	0.9700	C16A—H16A	0.9300
C10A—C11A	1.523 (3)	O2B—C12B	1.249 (2)
C10A—H10A	0.9700	O3B—N2B	1.232 (2)
C10A—H10B	0.9700	O4B—N2B	1.228 (2)
C11A—H11A	0.9700	O5B—N3B	1.236 (2)
C11A—H11B	0.9700	O6B—N3B	1.238 (2)
Cl1B—C3B	1.7405 (19)	O7B—N4B	1.227 (2)
O1B—C7B	1.428 (2)	O8B—N4B	1.229 (2)
O1B—H1B	0.8200	N2B—C13B	1.457 (2)
N1B—C9B	1.492 (3)	N3B—C15B	1.447 (2)
N1B—C10B	1.493 (2)	N4B—C17B	1.441 (3)
N1B—H1BB	0.9000	C12B—C13B	1.450 (3)
N1B—H1BC	0.9000	C12B—C17B	1.454 (2)
C1B—C6B	1.390 (2)	C13B—C14B	1.375 (3)
C1B—C2B	1.393 (3)	C14B—C15B	1.395 (3)
C1B—H1BA	0.9300	C14B—H14B	0.9300
C2B—C3B	1.377 (3)	C15B—C16B	1.379 (3)
C2B—H2BA	0.9300	C16B—C17B	1.391 (3)
C3B—C4B	1.396 (3)	C16B—H16B	0.9300
C4B—C5B	1.388 (3)	S1—O9	1.5076 (16)
C4B—H4BA	0.9300	S1—C19	1.780 (2)
C5B—C6B	1.400 (3)	S1—C18	1.789 (3)
C5B—H5BA	0.9300	C18—H18A	0.9600
C6B—C7B	1.526 (2)	C18—H18B	0.9600
C7B—C8B	1.536 (2)	C18—H18C	0.9600
C7B—C11B	1.538 (2)	C19—H19A	0.9600
C8B—C9B	1.529 (3)	C19—H19B	0.9600
C8B—H8BA	0.9700	C19—H19C	0.9600
C8B—H8BB	0.9700
C7A—O1A—H1A	109.5	C7B—C8B—H8BB	109.4
C10A—N1A—C9A	112.02 (14)	H8BA—C8B—H8BB	108.0
C10A—N1A—H1AB	109.2	N1B—C9B—C8B	109.85 (15)
C9A—N1A—H1AB	109.2	N1B—C9B—H9BA	109.7
C10A—N1A—H1AC	109.2	C8B—C9B—H9BA	109.7
C9A—N1A—H1AC	109.2	N1B—C9B—H9BB	109.7
H1AB—N1A—H1AC	107.9	C8B—C9B—H9BB	109.7
C6A—C1A—C2A	121.15 (17)	H9BA—C9B—H9BB	108.2
C6A—C1A—H1AA	119.4	N1B—C10B—C11B	109.90 (15)
C2A—C1A—H1AA	119.4	N1B—C10B—H10C	109.7
C3A—C2A—C1A	118.65 (17)	C11B—C10B—H10C	109.7
C3A—C2A—H2AA	120.7	N1B—C10B—H10D	109.7
C1A—C2A—H2AA	120.7	C11B—C10B—H10D	109.7
C2A—C3A—C4A	121.56 (17)	H10C—C10B—H10D	108.2
C2A—C3A—Cl1A	119.02 (14)	C10B—C11B—C7B	110.79 (15)
C4A—C3A—Cl1A	119.41 (14)	C10B—C11B—H11C	109.5
C5A—C4A—C3A	118.80 (17)	C7B—C11B—H11C	109.5
C5A—C4A—H4AA	120.6	C10B—C11B—H11D	109.5
C3A—C4A—H4AA	120.6	C7B—C11B—H11D	109.5
C4A—C5A—C6A	121.80 (17)	H11C—C11B—H11D	108.1
C4A—C5A—H5AA	119.1	O4A—N2A—O3A	121.54 (17)
C6A—C5A—H5AA	119.1	O4A—N2A—C13A	118.85 (16)
C1A—C6A—C5A	117.99 (16)	O3A—N2A—C13A	119.60 (15)
C1A—C6A—C7A	123.39 (16)	O6A—N3A—O5A	123.05 (19)
C5A—C6A—C7A	118.56 (16)	O6A—N3A—C15A	118.24 (17)
O1A—C7A—C6A	108.89 (13)	O5A—N3A—C15A	118.66 (18)
O1A—C7A—C8A	110.52 (14)	O8A—N4A—O7A	123.30 (17)
C6A—C7A—C8A	110.63 (14)	O8A—N4A—C17A	119.63 (17)
O1A—C7A—C11A	105.28 (14)	O7A—N4A—C17A	117.07 (17)
C6A—C7A—C11A	112.23 (14)	O2A—C12A—C13A	125.20 (17)
C8A—C7A—C11A	109.16 (14)	O2A—C12A—C17A	122.95 (16)
C9A—C8A—C7A	112.54 (15)	C13A—C12A—C17A	111.85 (15)
C9A—C8A—H8AA	109.1	C14A—C13A—N2A	115.26 (15)
C7A—C8A—H8AA	109.1	C14A—C13A—C12A	124.41 (17)
C9A—C8A—H8AB	109.1	N2A—C13A—C12A	120.24 (16)
C7A—C8A—H8AB	109.1	C13A—C14A—C15A	118.76 (16)
H8AA—C8A—H8AB	107.8	C13A—C14A—H14A	120.6
N1A—C9A—C8A	110.14 (15)	C15A—C14A—H14A	120.6
N1A—C9A—H9AA	109.6	C14A—C15A—C16A	121.66 (17)
C8A—C9A—H9AA	109.6	C14A—C15A—N3A	118.66 (16)
N1A—C9A—H9AB	109.6	C16A—C15A—N3A	119.52 (17)
C8A—C9A—H9AB	109.6	C17A—C16A—C15A	119.20 (17)
H9AA—C9A—H9AB	108.1	C17A—C16A—H16A	120.4
N1A—C10A—C11A	109.57 (16)	C15A—C16A—H16A	120.4
N1A—C10A—H10A	109.8	C16A—C17A—C12A	124.09 (16)
C11A—C10A—H10A	109.8	C16A—C17A—N4A	116.64 (17)
N1A—C10A—H10B	109.8	C12A—C17A—N4A	119.17 (16)
C11A—C10A—H10B	109.8	O4B—N2B—O3B	123.28 (17)
H10A—C10A—H10B	108.2	O4B—N2B—C13B	117.86 (16)
C10A—C11A—C7A	110.63 (15)	O3B—N2B—C13B	118.85 (16)
C10A—C11A—H11A	109.5	O5B—N3B—O6B	123.47 (18)
C7A—C11A—H11A	109.5	O5B—N3B—C15B	117.93 (17)
C10A—C11A—H11B	109.5	O6B—N3B—C15B	118.58 (17)
C7A—C11A—H11B	109.5	O7B—N4B—O8B	121.23 (18)
H11A—C11A—H11B	108.1	O7B—N4B—C17B	118.65 (16)
C7B—O1B—H1B	109.5	O8B—N4B—C17B	120.11 (15)
C9B—N1B—C10B	112.08 (14)	O2B—C12B—C13B	122.76 (16)
C9B—N1B—H1BB	109.2	O2B—C12B—C17B	125.56 (17)
C10B—N1B—H1BB	109.2	C13B—C12B—C17B	111.68 (15)
C9B—N1B—H1BC	109.2	C14B—C13B—C12B	124.71 (16)
C10B—N1B—H1BC	109.2	C14B—C13B—N2B	116.66 (17)
H1BB—N1B—H1BC	107.9	C12B—C13B—N2B	118.45 (16)
C6B—C1B—C2B	121.22 (18)	C13B—C14B—C15B	118.81 (17)
C6B—C1B—H1BA	119.4	C13B—C14B—H14B	120.6
C2B—C1B—H1BA	119.4	C15B—C14B—H14B	120.6
C3B—C2B—C1B	119.16 (17)	C16B—C15B—C14B	121.65 (17)
C3B—C2B—H2BA	120.4	C16B—C15B—N3B	118.75 (16)
C1B—C2B—H2BA	120.4	C14B—C15B—N3B	119.41 (17)
C2B—C3B—C4B	121.36 (17)	C15B—C16B—C17B	118.73 (16)
C2B—C3B—Cl1B	118.64 (14)	C15B—C16B—H16B	120.6
C4B—C3B—Cl1B	119.99 (15)	C17B—C16B—H16B	120.6
C5B—C4B—C3B	118.51 (18)	C16B—C17B—N4B	115.28 (15)
C5B—C4B—H4BA	120.7	C16B—C17B—C12B	124.34 (17)
C3B—C4B—H4BA	120.7	N4B—C17B—C12B	120.27 (16)
C4B—C5B—C6B	121.41 (16)	O9—S1—C19	107.14 (10)
C4B—C5B—H5BA	119.3	O9—S1—C18	106.33 (12)
C6B—C5B—H5BA	119.3	C19—S1—C18	97.27 (15)
C1B—C6B—C5B	118.31 (17)	S1—C18—H18A	109.5
C1B—C6B—C7B	120.55 (16)	S1—C18—H18B	109.5
C5B—C6B—C7B	121.12 (15)	H18A—C18—H18B	109.5
O1B—C7B—C6B	110.62 (14)	S1—C18—H18C	109.5
O1B—C7B—C8B	105.39 (14)	H18A—C18—H18C	109.5
C6B—C7B—C8B	110.72 (14)	H18B—C18—H18C	109.5
O1B—C7B—C11B	109.05 (14)	S1—C19—H19A	109.5
C6B—C7B—C11B	111.22 (14)	S1—C19—H19B	109.5
C8B—C7B—C11B	109.66 (14)	H19A—C19—H19B	109.5
C9B—C8B—C7B	111.24 (15)	S1—C19—H19C	109.5
C9B—C8B—H8BA	109.4	H19A—C19—H19C	109.5
C7B—C8B—H8BA	109.4	H19B—C19—H19C	109.5
C9B—C8B—H8BB	109.4
C6A—C1A—C2A—C3A	−0.1 (3)	O4A—N2A—C13A—C12A	−163.82 (17)
C1A—C2A—C3A—C4A	−1.7 (3)	O3A—N2A—C13A—C12A	17.0 (3)
C1A—C2A—C3A—Cl1A	177.09 (15)	O2A—C12A—C13A—C14A	−178.98 (18)
C2A—C3A—C4A—C5A	1.7 (3)	C17A—C12A—C13A—C14A	1.6 (2)
Cl1A—C3A—C4A—C5A	−177.14 (16)	O2A—C12A—C13A—N2A	4.4 (3)
C3A—C4A—C5A—C6A	0.3 (3)	C17A—C12A—C13A—N2A	−175.00 (15)
C2A—C1A—C6A—C5A	2.0 (3)	N2A—C13A—C14A—C15A	174.83 (16)
C2A—C1A—C6A—C7A	−175.00 (18)	C12A—C13A—C14A—C15A	−1.9 (3)
C4A—C5A—C6A—C1A	−2.1 (3)	C13A—C14A—C15A—C16A	0.6 (3)
C4A—C5A—C6A—C7A	175.07 (18)	C13A—C14A—C15A—N3A	−174.74 (17)
C1A—C6A—C7A—O1A	118.45 (19)	O6A—N3A—C15A—C14A	172.6 (2)
C5A—C6A—C7A—O1A	−58.5 (2)	O5A—N3A—C15A—C14A	−4.8 (3)
C1A—C6A—C7A—C8A	−119.90 (19)	O6A—N3A—C15A—C16A	−2.9 (3)
C5A—C6A—C7A—C8A	63.1 (2)	O5A—N3A—C15A—C16A	179.7 (2)
C1A—C6A—C7A—C11A	2.3 (2)	C14A—C15A—C16A—C17A	0.9 (3)
C5A—C6A—C7A—C11A	−174.66 (16)	N3A—C15A—C16A—C17A	176.16 (17)
O1A—C7A—C8A—C9A	−60.77 (19)	C15A—C16A—C17A—C12A	−1.1 (3)
C6A—C7A—C8A—C9A	178.54 (15)	C15A—C16A—C17A—N4A	−177.49 (16)
C11A—C7A—C8A—C9A	54.6 (2)	O2A—C12A—C17A—C16A	−179.49 (18)
C10A—N1A—C9A—C8A	56.6 (2)	C13A—C12A—C17A—C16A	0.0 (2)
C7A—C8A—C9A—N1A	−54.3 (2)	O2A—C12A—C17A—N4A	−3.2 (3)
C9A—N1A—C10A—C11A	−59.5 (2)	C13A—C12A—C17A—N4A	176.24 (15)
N1A—C10A—C11A—C7A	59.51 (19)	O8A—N4A—C17A—C16A	−151.85 (18)
O1A—C7A—C11A—C10A	61.98 (18)	O7A—N4A—C17A—C16A	28.1 (2)
C6A—C7A—C11A—C10A	−179.71 (15)	O8A—N4A—C17A—C12A	31.6 (2)
C8A—C7A—C11A—C10A	−56.7 (2)	O7A—N4A—C17A—C12A	−148.48 (18)
C6B—C1B—C2B—C3B	−0.2 (3)	O2B—C12B—C13B—C14B	177.23 (18)
C1B—C2B—C3B—C4B	0.8 (3)	C17B—C12B—C13B—C14B	−3.2 (2)
C1B—C2B—C3B—Cl1B	−178.29 (15)	O2B—C12B—C13B—N2B	2.3 (3)
C2B—C3B—C4B—C5B	−0.2 (3)	C17B—C12B—C13B—N2B	−178.07 (14)
Cl1B—C3B—C4B—C5B	178.96 (14)	O4B—N2B—C13B—C14B	−33.8 (2)
C3B—C4B—C5B—C6B	−1.2 (3)	O3B—N2B—C13B—C14B	145.35 (18)
C2B—C1B—C6B—C5B	−1.1 (3)	O4B—N2B—C13B—C12B	141.56 (19)
C2B—C1B—C6B—C7B	177.12 (17)	O3B—N2B—C13B—C12B	−39.3 (2)
C4B—C5B—C6B—C1B	1.8 (3)	C12B—C13B—C14B—C15B	3.2 (3)
C4B—C5B—C6B—C7B	−176.40 (16)	N2B—C13B—C14B—C15B	178.19 (15)
C1B—C6B—C7B—O1B	5.6 (2)	C13B—C14B—C15B—C16B	−1.1 (3)
C5B—C6B—C7B—O1B	−176.22 (15)	C13B—C14B—C15B—N3B	−175.95 (16)
C1B—C6B—C7B—C8B	−110.87 (19)	O5B—N3B—C15B—C16B	−179.11 (19)
C5B—C6B—C7B—C8B	67.3 (2)	O6B—N3B—C15B—C16B	−0.8 (3)
C1B—C6B—C7B—C11B	126.93 (18)	O5B—N3B—C15B—C14B	−4.1 (3)
C5B—C6B—C7B—C11B	−54.9 (2)	O6B—N3B—C15B—C14B	174.24 (18)
O1B—C7B—C8B—C9B	62.18 (18)	C14B—C15B—C16B—C17B	−0.7 (3)
C6B—C7B—C8B—C9B	−178.17 (15)	N3B—C15B—C16B—C17B	174.20 (16)
C11B—C7B—C8B—C9B	−55.1 (2)	C15B—C16B—C17B—N4B	−175.51 (16)
C10B—N1B—C9B—C8B	−58.6 (2)	C15B—C16B—C17B—C12B	0.5 (3)
C7B—C8B—C9B—N1B	56.3 (2)	O7B—N4B—C17B—C16B	−20.3 (3)
C9B—N1B—C10B—C11B	59.6 (2)	O8B—N4B—C17B—C16B	159.0 (2)
N1B—C10B—C11B—C7B	−57.6 (2)	O7B—N4B—C17B—C12B	163.47 (18)
O1B—C7B—C11B—C10B	−59.23 (19)	O8B—N4B—C17B—C12B	−17.2 (3)
C6B—C7B—C11B—C10B	178.51 (14)	O2B—C12B—C17B—C16B	−179.16 (18)
C8B—C7B—C11B—C10B	55.7 (2)	C13B—C12B—C17B—C16B	1.2 (2)
O4A—N2A—C13A—C14A	19.3 (2)	O2B—C12B—C17B—N4B	−3.3 (3)
O3A—N2A—C13A—C14A	−159.87 (18)	C13B—C12B—C17B—N4B	177.10 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1AB···O7Bi	0.90	2.44	3.030 (2)	123
N1A—H1AB···O8Bi	0.90	2.15	3.048 (2)	176
O1A—H1A···O1Bii	0.82	2.14	2.8642 (19)	148
O1B—H1B···O9iii	0.82	1.83	2.629 (2)	165
N1A—H1AC···O2A	0.90	1.83	2.704 (2)	162
N1A—H1AC···O3A	0.90	2.30	2.846 (2)	119
N1B—H1BB···O3Aiv	0.90	2.15	3.044 (2)	171
N1B—H1BB···O4Aiv	0.90	2.52	3.101 (2)	123
N1B—H1BC···O2B	0.90	1.84	2.714 (2)	162
C4A—H4AA···O4Av	0.93	2.51	3.311 (2)	145
C5A—H5AA···O1Bii	0.93	2.52	3.313 (2)	143
C8A—H8AA···O9vi	0.97	2.58	3.479 (2)	155
C9A—H9AB···O4Bvii	0.97	2.59	3.469 (3)	151
C11A—H11A···O2A	0.97	2.55	3.261 (2)	130
C11A—H11B···O4B	0.97	2.59	3.258 (3)	126
C2B—H2BA···O7Bv	0.93	2.60	3.361 (3)	140
C14B—H14B···O6Ai	0.93	2.45	3.335 (3)	160
C5B—H5BA···O3B	0.93	2.54	3.424 (2)	160
C16A—H16A···O5Biv	0.93	2.51	3.418 (3)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1AB⋯O7Bi	0.90	2.44	3.030 (2)	123
N1A—H1AB⋯O8Bi	0.90	2.15	3.048 (2)	176
O1A—H1A⋯O1Bii	0.82	2.14	2.8642 (19)	148
O1B—H1B⋯O9iii	0.82	1.83	2.629 (2)	165
N1A—H1AC⋯O2A	0.90	1.83	2.704 (2)	162
N1A—H1AC⋯O3A	0.90	2.30	2.846 (2)	119
N1B—H1BB⋯O3Aiv	0.90	2.15	3.044 (2)	171
N1B—H1BB⋯O4Aiv	0.90	2.52	3.101 (2)	123
N1B—H1BC⋯O2B	0.90	1.84	2.714 (2)	162
C4A—H4AA⋯O4Av	0.93	2.51	3.311 (2)	145
C5A—H5AA⋯O1Bii	0.93	2.52	3.313 (2)	143
C8A—H8AA⋯O9vi	0.97	2.58	3.479 (2)	155
C9A—H9AB⋯O4Bvii	0.97	2.59	3.469 (3)	151
C11A—H11A⋯O2A	0.97	2.55	3.261 (2)	130
C11A—H11B⋯O4B	0.97	2.59	3.258 (3)	126
C2B—H2BA⋯O7Bv	0.93	2.60	3.361 (3)	140
C14B—H14B⋯O6Ai	0.93	2.45	3.335 (3)	160
C5B—H5BA⋯O3B	0.93	2.54	3.424 (2)	160
C16A—H16A⋯O5Biv	0.93	2.51	3.418 (3)	166

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